WO1999014216A1 - Substituted 3(-1,2-benzisothiazol or isoxazol-5 yl)-substituted pyrimidine as herbicides - Google Patents
Substituted 3(-1,2-benzisothiazol or isoxazol-5 yl)-substituted pyrimidine as herbicides Download PDFInfo
- Publication number
- WO1999014216A1 WO1999014216A1 PCT/US1998/019251 US9819251W WO9914216A1 WO 1999014216 A1 WO1999014216 A1 WO 1999014216A1 US 9819251 W US9819251 W US 9819251W WO 9914216 A1 WO9914216 A1 WO 9914216A1
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- WO
- WIPO (PCT)
- Prior art keywords
- groups
- group
- alkyl
- optionally substituted
- alkoxy
- Prior art date
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- 239000004009 herbicide Substances 0.000 title description 13
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 title description 5
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 209
- 238000000034 method Methods 0.000 claims abstract description 67
- 241000196324 Embryophyta Species 0.000 claims abstract description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 345
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 343
- -1 cyano, nitro, amino, hydroxyl Chemical group 0.000 claims description 327
- 125000005843 halogen group Chemical group 0.000 claims description 313
- 229910052739 hydrogen Inorganic materials 0.000 claims description 289
- 239000001257 hydrogen Substances 0.000 claims description 288
- 229910052736 halogen Inorganic materials 0.000 claims description 280
- 150000002367 halogens Chemical group 0.000 claims description 280
- 150000002431 hydrogen Chemical group 0.000 claims description 227
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 227
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 202
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 188
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 186
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 168
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 163
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 156
- 239000007787 solid Substances 0.000 claims description 122
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 119
- 239000000203 mixture Substances 0.000 claims description 99
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 96
- 125000000623 heterocyclic group Chemical group 0.000 claims description 93
- 125000002950 monocyclic group Chemical group 0.000 claims description 92
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 80
- 125000002619 bicyclic group Chemical group 0.000 claims description 73
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 70
- 125000003844 furanonyl group Chemical group 0.000 claims description 58
- 238000002360 preparation method Methods 0.000 claims description 56
- 229910052757 nitrogen Inorganic materials 0.000 claims description 51
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 48
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 47
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
- 229910052783 alkali metal Inorganic materials 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
- 150000001340 alkali metals Chemical class 0.000 claims description 40
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 40
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 40
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 39
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 39
- 125000004076 pyridyl group Chemical group 0.000 claims description 38
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 37
- 229910052725 zinc Inorganic materials 0.000 claims description 37
- 239000011701 zinc Substances 0.000 claims description 37
- 125000001544 thienyl group Chemical group 0.000 claims description 36
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 35
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 35
- 239000010949 copper Substances 0.000 claims description 35
- 229910052802 copper Inorganic materials 0.000 claims description 35
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 35
- 229910052759 nickel Inorganic materials 0.000 claims description 35
- 229910052709 silver Inorganic materials 0.000 claims description 35
- 239000004332 silver Substances 0.000 claims description 35
- 229910017052 cobalt Inorganic materials 0.000 claims description 34
- 239000010941 cobalt Substances 0.000 claims description 34
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 150000002148 esters Chemical class 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 31
- 239000002585 base Substances 0.000 claims description 30
- 125000004043 oxo group Chemical group O=* 0.000 claims description 30
- 239000000460 chlorine Substances 0.000 claims description 28
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 28
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 28
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 22
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 19
- 125000002541 furyl group Chemical group 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 18
- 239000011593 sulfur Substances 0.000 claims description 18
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 18
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 17
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 16
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
- 125000005646 oximino group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 14
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 14
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims description 14
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 14
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical group C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 14
- DQPULKJUSYSTBM-UHFFFAOYSA-N 3-[3-(hydroxymethyl)-1,2-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(SN=C2CO)C2=C1 DQPULKJUSYSTBM-UHFFFAOYSA-N 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 230000003287 optical effect Effects 0.000 claims description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 10
- 229930192474 thiophene Natural products 0.000 claims description 10
- 210000000056 organ Anatomy 0.000 claims description 9
- 230000001902 propagating effect Effects 0.000 claims description 9
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 8
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 8
- 125000005336 allyloxy group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 8
- KCYUZABVXQYVDE-UHFFFAOYSA-N 5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-n-propan-2-ylsulfonyl-1,2-benzothiazole-3-carboxamide Chemical compound C1=C2C(C(=O)NS(=O)(=O)C(C)C)=NSC2=CC=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O KCYUZABVXQYVDE-UHFFFAOYSA-N 0.000 claims description 7
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 7
- 240000007594 Oryza sativa Species 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 239000012039 electrophile Substances 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- VXRWWXRYBXFAQT-UHFFFAOYSA-N n-(dimethylsulfamoyl)-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1=C2C(C(=O)NS(=O)(=O)N(C)C)=NSC2=CC=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O VXRWWXRYBXFAQT-UHFFFAOYSA-N 0.000 claims description 7
- KUVVDQSHRGBNOB-UHFFFAOYSA-N n-ethylsulfonyl-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1=C2C(C(=O)NS(=O)(=O)CC)=NSC2=CC=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O KUVVDQSHRGBNOB-UHFFFAOYSA-N 0.000 claims description 7
- 239000002689 soil Substances 0.000 claims description 7
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 7
- NSBWJCIZOONNQY-UHFFFAOYSA-N 1-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound FC(F)(F)N1C=CC(=O)NC1=O NSBWJCIZOONNQY-UHFFFAOYSA-N 0.000 claims description 6
- RHTUQTQNJSARMD-UHFFFAOYSA-N 5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-n-methylsulfonyl-1,2-benzothiazole-3-carboxamide Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(SN=C2C(=O)NS(C)(=O)=O)C2=C1 RHTUQTQNJSARMD-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 235000007164 Oryza sativa Nutrition 0.000 claims description 6
- 241000209140 Triticum Species 0.000 claims description 6
- 235000021307 Triticum Nutrition 0.000 claims description 6
- 240000008042 Zea mays Species 0.000 claims description 6
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 6
- 235000013339 cereals Nutrition 0.000 claims description 6
- 235000005822 corn Nutrition 0.000 claims description 6
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 claims description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- 235000009566 rice Nutrition 0.000 claims description 6
- WKIOQNPKWHHOOO-UHFFFAOYSA-N 2,5-dihydrooxazin-6-one Chemical compound O=C1CC=CNO1 WKIOQNPKWHHOOO-UHFFFAOYSA-N 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- MWLNFERZNNTDAB-UHFFFAOYSA-N 5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-n-(propan-2-ylsulfamoyl)-1,2-benzothiazole-3-carboxamide Chemical compound C1=C2C(C(=O)NS(=O)(=O)NC(C)C)=NSC2=CC=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O MWLNFERZNNTDAB-UHFFFAOYSA-N 0.000 claims description 5
- ZVHVSBUADWJVNH-UHFFFAOYSA-N methyl 5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carboxylate Chemical compound C1=C2C(C(=O)OC)=NSC2=CC=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O ZVHVSBUADWJVNH-UHFFFAOYSA-N 0.000 claims description 5
- RDEZGFOPFILMHL-UHFFFAOYSA-N n-[di(propan-2-yl)sulfamoyl]-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1=C2C(C(=O)NS(=O)(=O)N(C(C)C)C(C)C)=NSC2=CC=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O RDEZGFOPFILMHL-UHFFFAOYSA-N 0.000 claims description 5
- MIIQJAUWHSUTIT-UHFFFAOYSA-N 1,2-oxazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=NO1 MIIQJAUWHSUTIT-UHFFFAOYSA-N 0.000 claims description 4
- SMNDYUVBFMFKNZ-UHFFFAOYSA-M 2-furoate Chemical compound [O-]C(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-M 0.000 claims description 4
- SILJXCPCJNNHNV-UHFFFAOYSA-N 3-[3-(dibromomethyl)-1,2-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(SN=C2C(Br)Br)C2=C1 SILJXCPCJNNHNV-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 244000068988 Glycine max Species 0.000 claims description 4
- 235000010469 Glycine max Nutrition 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- 229910052731 fluorine Chemical group 0.000 claims description 4
- RMIODHQZRUFFFF-UHFFFAOYSA-M methoxyacetate Chemical compound COCC([O-])=O RMIODHQZRUFFFF-UHFFFAOYSA-M 0.000 claims description 4
- QERYCTSHXKAMIS-UHFFFAOYSA-M thiophene-2-carboxylate Chemical compound [O-]C(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-M 0.000 claims description 4
- TURQCINHOUHXNR-UHFFFAOYSA-N 2-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]acetonitrile Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(SN=C2CC#N)C2=C1 TURQCINHOUHXNR-UHFFFAOYSA-N 0.000 claims description 3
- BWNRLKZRCYLAGC-UHFFFAOYSA-N 3-[3-(3-methoxy-4-methylphenyl)-1,2-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound C1=C(C)C(OC)=CC(C=2C3=CC(=CC=C3SN=2)N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 BWNRLKZRCYLAGC-UHFFFAOYSA-N 0.000 claims description 3
- HZCDWHDRHCFBLV-UHFFFAOYSA-N 3-[3-(4-ethylphenyl)-1,2-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound C1=CC(CC)=CC=C1C1=NSC2=CC=C(N3C(N(C)C(=CC3=O)C(F)(F)F)=O)C=C12 HZCDWHDRHCFBLV-UHFFFAOYSA-N 0.000 claims description 3
- VTZCNZXSRMHVAN-UHFFFAOYSA-N 3-[3-(4-methoxy-3-methylphenyl)-1,2-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound C1=C(C)C(OC)=CC=C1C1=NSC2=CC=C(N3C(N(C)C(=CC3=O)C(F)(F)F)=O)C=C12 VTZCNZXSRMHVAN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 3
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 3
- 125000004970 halomethyl group Chemical group 0.000 claims description 3
- 230000002363 herbicidal effect Effects 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 125000005543 phthalimide group Chemical group 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- VYAFKMIMRJWLNW-UHFFFAOYSA-N 4-(propan-2-ylsulfamoyl)-1,2-benzothiazole-3-carboxamide Chemical compound CC(C)NS(=O)(=O)C1=CC=CC2=C1C(C(N)=O)=NS2 VYAFKMIMRJWLNW-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- CHTJXIQLKYRYKC-UHFFFAOYSA-N CN1C(N(C(C=C1C(F)(F)F)=O)C=1C=CC2=C(C(=NS2)C2=C(C=CC(=C2)OCC(=O)OCC(F)(F)F)C)C1)=O Chemical compound CN1C(N(C(C=C1C(F)(F)F)=O)C=1C=CC2=C(C(=NS2)C2=C(C=CC(=C2)OCC(=O)OCC(F)(F)F)C)C1)=O CHTJXIQLKYRYKC-UHFFFAOYSA-N 0.000 claims description 2
- 244000038559 crop plants Species 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- JAIYHPUVNLVDNJ-UHFFFAOYSA-N n-benzylsulfonyl-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(SN=C2C(=O)NS(=O)(=O)CC=3C=CC=CC=3)C2=C1 JAIYHPUVNLVDNJ-UHFFFAOYSA-N 0.000 claims description 2
- OKWBLVIQIQGPNR-UHFFFAOYSA-N n-methoxy-2-[4-methyl-3-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]phenoxy]acetamide Chemical compound CONC(=O)COC1=CC=C(C)C(C=2C3=CC(=CC=C3SN=2)N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 OKWBLVIQIQGPNR-UHFFFAOYSA-N 0.000 claims description 2
- XDUZZPZPRQWNGH-UHFFFAOYSA-N 3-[3-(2-methoxyphenyl)-1,2-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound COC1=CC=CC=C1C1=NSC2=CC=C(N3C(N(C)C(=CC3=O)C(F)(F)F)=O)C=C12 XDUZZPZPRQWNGH-UHFFFAOYSA-N 0.000 claims 3
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims 3
- LXXMNJGULZATIV-UHFFFAOYSA-N CN1C(N(C(C=C1C(F)(F)F)=O)C=1C=CC2=C(C(=NS2)C2=C(C=CC(=C2)OCC(=O)OC(C)C)C)C1)=O Chemical compound CN1C(N(C(C=C1C(F)(F)F)=O)C=1C=CC2=C(C(=NS2)C2=C(C=CC(=C2)OCC(=O)OC(C)C)C)C1)=O LXXMNJGULZATIV-UHFFFAOYSA-N 0.000 claims 3
- IMBUBZIBJJGWMN-UHFFFAOYSA-N 2-[2-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]phenoxy]acetic acid Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(SN=C2C=3C(=CC=CC=3)OCC(O)=O)C2=C1 IMBUBZIBJJGWMN-UHFFFAOYSA-N 0.000 claims 2
- NQJNXZVTGPQFCR-UHFFFAOYSA-N 2-[4-methyl-3-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]phenoxy]-n-methylsulfonylacetamide Chemical compound CC1=CC=C(OCC(=O)NS(C)(=O)=O)C=C1C1=NSC2=CC=C(N3C(N(C)C(=CC3=O)C(F)(F)F)=O)C=C12 NQJNXZVTGPQFCR-UHFFFAOYSA-N 0.000 claims 2
- PARRQMVSGNIUGW-UHFFFAOYSA-N CN1C(N(C(C=C1C(F)(F)F)=O)C=1C=CC2=C(C(=NO2)C2=C(C=CC(=C2)OCC(=O)OCC#C)C)C1)=O Chemical compound CN1C(N(C(C=C1C(F)(F)F)=O)C=1C=CC2=C(C(=NO2)C2=C(C=CC(=C2)OCC(=O)OCC#C)C)C1)=O PARRQMVSGNIUGW-UHFFFAOYSA-N 0.000 claims 2
- XXMJERQBWVZHBM-UHFFFAOYSA-N methyl 2-[3-[6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzoxazol-3-yl]-4-methylphenoxy]acetate Chemical compound COC(=O)COC1=CC=C(C)C(C=2C3=CC(=C(F)C=C3ON=2)N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 XXMJERQBWVZHBM-UHFFFAOYSA-N 0.000 claims 2
- IPMYFDNZJWDKHI-UHFFFAOYSA-N methyl 2-[4,5-dimethyl-2-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]phenoxy]propanoate Chemical compound COC(=O)C(C)OC1=CC(C)=C(C)C=C1C1=NSC2=CC=C(N3C(N(C)C(=CC3=O)C(F)(F)F)=O)C=C12 IPMYFDNZJWDKHI-UHFFFAOYSA-N 0.000 claims 2
- ARIOPGOVCUCLEU-UHFFFAOYSA-N n-[(3-chlorophenyl)methylsulfonyl]-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(SN=C2C(=O)NS(=O)(=O)CC=3C=C(Cl)C=CC=3)C2=C1 ARIOPGOVCUCLEU-UHFFFAOYSA-N 0.000 claims 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- YBNCTQVBIVXSRW-UHFFFAOYSA-N prop-2-ynyl 2-[2-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]phenoxy]acetate Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(SN=C2C=3C(=CC=CC=3)OCC(=O)OCC#C)C2=C1 YBNCTQVBIVXSRW-UHFFFAOYSA-N 0.000 claims 2
- IABBFAWTTAULCO-UHFFFAOYSA-N 2-[2-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1C1=NSC2=CC=C(N3C(N(C)C(=CC3=O)C(F)(F)F)=O)C=C12 IABBFAWTTAULCO-UHFFFAOYSA-N 0.000 claims 1
- WTRHQQGDDODSRZ-UHFFFAOYSA-N 2-chloroethyl 2-[4-methyl-3-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]phenoxy]propanoate Chemical compound ClCCOC(=O)C(C)OC1=CC=C(C)C(C=2C3=CC(=CC=C3SN=2)N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 WTRHQQGDDODSRZ-UHFFFAOYSA-N 0.000 claims 1
- QEVDUOVJUHHSIL-UHFFFAOYSA-N 3-phenylprop-2-ynyl 2-[4-methyl-3-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]phenoxy]acetate Chemical compound CN1C(N(C(C=C1C(F)(F)F)=O)C=1C=CC2=C(C(=NS2)C2=C(C=CC(=C2)OCC(=O)OCC#CC2=CC=CC=C2)C)C1)=O QEVDUOVJUHHSIL-UHFFFAOYSA-N 0.000 claims 1
- WQUBEIMCFHCJCO-AWCRTANDSA-N 4-amino-n-{4-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-hydroxy-1-isobutyl-5-phenyl-pentyl}-benzamide Chemical compound C([C@@H]([C@@H](O)C[C@H](CC(C)C)NC(=O)C=1C=C(N)C=CC=1)NC(=O)COC=1C(=CC=CC=1C)C)C1=CC=CC=C1 WQUBEIMCFHCJCO-AWCRTANDSA-N 0.000 claims 1
- NZHSMVSTWJMYLE-UHFFFAOYSA-N 5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-n-[(4-methylphenyl)methylsulfonyl]-1,2-benzothiazole-3-carboxamide Chemical compound C1=CC(C)=CC=C1CS(=O)(=O)NC(=O)C1=NSC2=CC=C(N3C(N(C)C(=CC3=O)C(F)(F)F)=O)C=C12 NZHSMVSTWJMYLE-UHFFFAOYSA-N 0.000 claims 1
- OEXVVGKAILRIHD-UHFFFAOYSA-N 6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carbaldehyde Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C(C(=C1)F)=CC2=C1SN=C2C=O OEXVVGKAILRIHD-UHFFFAOYSA-N 0.000 claims 1
- QIUOYHTVEPQZGW-UHFFFAOYSA-N 6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carboxylic acid Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C(C(=C1)F)=CC2=C1SN=C2C(O)=O QIUOYHTVEPQZGW-UHFFFAOYSA-N 0.000 claims 1
- UYUDXGQNFLWLDW-UHFFFAOYSA-N CN1C(N(C(C=C1C(F)(F)F)=O)C=1C=CC2=C(C(=NO2)C2=C(C=CC(=C2)OCC(=O)OC)C)C1)=O Chemical compound CN1C(N(C(C=C1C(F)(F)F)=O)C=1C=CC2=C(C(=NO2)C2=C(C=CC(=C2)OCC(=O)OC)C)C1)=O UYUDXGQNFLWLDW-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- HXQQOQCCBYJMHY-UHFFFAOYSA-N methyl 2-[2,4-dimethyl-6-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]phenoxy]acetate Chemical compound COC(=O)COC1=C(C)C=C(C)C=C1C1=NSC2=CC=C(N3C(N(C)C(=CC3=O)C(F)(F)F)=O)C=C12 HXQQOQCCBYJMHY-UHFFFAOYSA-N 0.000 claims 1
- VKIHIYDJWTUBTN-UHFFFAOYSA-N methyl 2-[4-[6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]-3-methylphenoxy]acetate Chemical compound COC(COC=1C=C(C(=CC=1)C1=NSC2=C1C=C(C(=C2)F)N1C(N(C(=CC1=O)C(F)(F)F)C)=O)C)=O VKIHIYDJWTUBTN-UHFFFAOYSA-N 0.000 claims 1
- WHHPDEBDOABGOO-UHFFFAOYSA-N n-benzylsulfonyl-6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C(C(=C1)F)=CC2=C1SN=C2C(=O)NS(=O)(=O)CC1=CC=CC=C1 WHHPDEBDOABGOO-UHFFFAOYSA-N 0.000 claims 1
- DMRKBTQZKOXGNF-UHFFFAOYSA-N n-benzylsulfonyl-n-(ethoxymethyl)-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C=1C=CC=CC=1CS(=O)(=O)N(COCC)C(=O)C(C1=C2)=NSC1=CC=C2N1C(=O)C=C(C(F)(F)F)N(C)C1=O DMRKBTQZKOXGNF-UHFFFAOYSA-N 0.000 claims 1
- XTRBDLAMPYVZQC-UHFFFAOYSA-N prop-2-ynyl 2-[4-methyl-3-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzothiazol-3-yl]phenoxy]acetate Chemical compound CN1C(N(C(C=C1C(F)(F)F)=O)C=1C=CC2=C(C(=NS2)C2=C(C=CC(=C2)OCC(=O)OCC#C)C)C1)=O XTRBDLAMPYVZQC-UHFFFAOYSA-N 0.000 claims 1
- ZSOHWXTYLCKMEI-UHFFFAOYSA-N prop-2-ynyl 2-[4-methyl-3-[5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-1,2-benzoxazol-3-yl]phenoxy]propanoate Chemical compound C#CCOC(=O)C(C)OC1=CC=C(C)C(C=2C3=CC(=CC=C3ON=2)N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 ZSOHWXTYLCKMEI-UHFFFAOYSA-N 0.000 claims 1
- 241001061127 Thione Species 0.000 abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 180
- 239000000243 solution Substances 0.000 description 92
- 238000010586 diagram Methods 0.000 description 76
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- 239000000047 product Substances 0.000 description 57
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 47
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
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- 238000004458 analytical method Methods 0.000 description 30
- 230000003595 spectral effect Effects 0.000 description 30
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- 238000004440 column chromatography Methods 0.000 description 20
- 238000010183 spectrum analysis Methods 0.000 description 20
- 239000012267 brine Substances 0.000 description 19
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
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- 239000000284 extract Substances 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 11
- 239000005457 ice water Substances 0.000 description 11
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 10
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- 125000005997 bromomethyl group Chemical group 0.000 description 9
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
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- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
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- 239000003638 chemical reducing agent Substances 0.000 description 5
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 5
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- 239000011734 sodium Substances 0.000 description 5
- 229910052721 tungsten Inorganic materials 0.000 description 5
- RHPWQBQNAZHUSY-UHFFFAOYSA-N (2-chloro-5-nitrophenyl)-(2-methoxy-5-methylphenyl)methanone Chemical compound COC1=CC=C(C)C=C1C(=O)C1=CC([N+]([O-])=O)=CC=C1Cl RHPWQBQNAZHUSY-UHFFFAOYSA-N 0.000 description 4
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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- IHEPGSXLLLUYDW-UHFFFAOYSA-N 2-chloro-4-fluoro-5-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=C(Cl)C=C1F IHEPGSXLLLUYDW-UHFFFAOYSA-N 0.000 description 3
- ATACZDPSSSRSTM-UHFFFAOYSA-N 3-[3-(bromomethyl)-1,2-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(SN=C2CBr)C2=C1 ATACZDPSSSRSTM-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- QZFIGQFIRSBAFE-UHFFFAOYSA-N 5-nitro-1,2-benzothiazol-3-one Chemical compound [O-][N+](=O)C1=CC=C2SNC(=O)C2=C1 QZFIGQFIRSBAFE-UHFFFAOYSA-N 0.000 description 3
- NPKARQNMFDJQQO-UHFFFAOYSA-N 5-nitro-1,2-benzoxazol-3-one Chemical compound C1=C([N+]([O-])=O)C=C2C(O)=NOC2=C1 NPKARQNMFDJQQO-UHFFFAOYSA-N 0.000 description 3
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 229910017912 NH2OH Inorganic materials 0.000 description 1
- 229910020656 PBr5 Inorganic materials 0.000 description 1
- 229910019201 POBr3 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical group CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229910007161 Si(CH3)3 Inorganic materials 0.000 description 1
- 229910021608 Silver(I) fluoride Inorganic materials 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 235000010716 Vigna mungo Nutrition 0.000 description 1
- 235000011453 Vigna umbellata Nutrition 0.000 description 1
- 230000009418 agronomic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005741 alkyl alkenyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000005466 alkylenyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- HFPGRVHMFSJMOL-UHFFFAOYSA-N dibromomethane Chemical compound Br[CH]Br HFPGRVHMFSJMOL-UHFFFAOYSA-N 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- NOFXBQRGSCZHSE-UHFFFAOYSA-N ethyl 2-(5-amino-1,2-benzothiazol-3-yl)acetate Chemical compound C1=C(N)C=C2C(CC(=O)OCC)=NSC2=C1 NOFXBQRGSCZHSE-UHFFFAOYSA-N 0.000 description 1
- JZVIYQRIMMOOLL-UHFFFAOYSA-N ethyl 2-(5-nitro-1,2-benzothiazol-3-yl)acetate Chemical compound C1=C([N+]([O-])=O)C=C2C(CC(=O)OCC)=NSC2=C1 JZVIYQRIMMOOLL-UHFFFAOYSA-N 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000000232 haloalkynyl group Chemical group 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- OTYIADUBGFZFSV-UHFFFAOYSA-N n-[4-(acetylsulfamoyl)phenyl]-2-[[2-[[4-(acetylsulfamoyl)phenyl]carbamoyl]phenyl]disulfanyl]benzamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1NC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(=O)NC1=CC=C(S(=O)(=O)NC(C)=O)C=C1 OTYIADUBGFZFSV-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 125000006412 propinylene group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229940048181 sodium sulfide nonahydrate Drugs 0.000 description 1
- UYCAUPASBSROMS-AWQJXPNKSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-][13C](=O)[13C](F)(F)F UYCAUPASBSROMS-AWQJXPNKSA-M 0.000 description 1
- WMDLZMCDBSJMTM-UHFFFAOYSA-M sodium;sulfanide;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[SH-] WMDLZMCDBSJMTM-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- NMLXKNNXODLJIN-UHFFFAOYSA-M zinc;carbanide;chloride Chemical compound [CH3-].[Zn+]Cl NMLXKNNXODLJIN-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
- C07F9/6541—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Definitions
- the present invention describes 3- (1, 2-benziso- thiazol- and isoxazol-5-yl) -2, 4 (IH, 3H) -pyrimidinedione or thione and 3- (1, 2-benzisothiazol- and isoxazol-5-yl) - 4(3H) -pyrimidinone or thione compounds which are useful as herbicidal agents .
- R is C ⁇ -C 6 alkyl, C ⁇ C g haloalkyl, C 3 -C 7 cycloalkyl,
- R x and R 2 are each independently hydrogen, " halogen, C j - ⁇ alkyl, C 3 -C 7 cycloalkyl, C ⁇ C j haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, OR 7 ,
- R x and R 2 when R x and R 2 are taken together with the atoms to which they are attached, they represent a four- to seven -membered saturated or unsaturated ring optionally interrupted by oxygen, sulfur or nitrogen, and optionally substituted with one to three methyl groups or one or more halogen atoms ;
- R 3 is halogen or A 2 R 1X ;
- X is hydrogen, halogen or C- ⁇ -C ⁇ lkyl;
- X 1 is hydrogen, halogen, C- ⁇ alkyl, C ⁇ haloalkyl, C j -C ⁇ lkoxy or C ⁇ haloalkoxy ;
- Z is 0 or S(0) m ;
- Y is halogen , cyano , R 12 , X 2 R 12 , X 3 R 12 , X 2 X 3 R 12 or X 3 X 2 R 12 ;
- X 2 is 0 , S ( 0 ) p or NR 13 ;
- R / R 5 1 R 6 ' ⁇ 7 ' R 8 , R 9 , R 10 / Rii a a>nd R l4 are each independently hydrogen, C ⁇ alkyl, C 3 -C 7 cycloalkyl, C 2 -C 8 - alkoxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or benzyl;
- R 12 is hydrogen, a C j -C 8 lkyl, C 3 -C 7 cycloalkyl, C 2 -C 8 alkenyl,
- each group is optionally substituted with any combination of one to six halogen atoms, one to three C ⁇ C ⁇ alko y groups optionally substituted with one C j -C j alkoxy, benzyloxy or C ⁇ -C 6 alkylthio group, one or two C ⁇ C ⁇ haloalkoxy groups, one or two NR 1S R 16 groups, one to three S(0) q R 17 groups, one or two cyano groups , one or two C 3 -C 7 cycloalkyl groups, one thiocyano group, one 0(S0 2 )R 17 group, one 0(N0 2 ) group, one or two C(0)R 18 groups, one or two C0 2 R 19 groups, one or two C(0)SR 19 groups, one or two C(O)NR 20 R 21 groups , one to three X 4 R 22 groups , one or two P(0)(OR
- C 1 -C 4 alkyl groups one to three C 1 -C 4 alkoxy groups, one C 3 -C 6 cycloalkyl group, one C ⁇ -C 4 haloalkyl group, one C 1 -C 4 alkylthio group, one cyano group, one nitro group, one C(0)R 25 group, one C0 2 R 26 group, one X 4 R 22 group, one
- C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, or one 5- to 12-membered monocyclic or fused bicyclic, heterocyclic ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C l -C 4 haloalkylsulfonyl groups, C 3 -C 20 alkenyl optionally substituted with one to three halogen atoms, one hydroxyl group, one C.-C.alkoxy, C0 2 R 32 , C(0)R 33 , C(A 4 R J4 ) 2 , C(0)NR 35 R 36 , C(0)ON CR 37 R 38 , C(0)NR 35 OR 23 , cyano or 2-dioxolanyl group, or
- C.-C.alkyl groups one to three -C ⁇ C.haloalkyl groups, one to three C ⁇ -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, phenyl optionally substituted with any combination of one to three halogen atoms, one to three
- C ⁇ C.alkyl groups one to three C ⁇ -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one C0 2 R 26 group, C(0)R 43 , or C0 2 R 42 ;
- R 16 and R 21 are each independently hydrogen, C j -C ⁇ lkyl,
- C 1 -C 4 alkyl groups one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups or one X 4 R 22 group, or phenyl optionally substituted with any combination of one to three halogen atoms, one to three
- R 19 and R 26 are each independently hydrogen, C- ⁇ C ⁇ alkyl, C ⁇ -C 8 haloalkyl, C 3 -C 7 cycloalkyl, C 3 -C 7 halocycloalkyl, C 3 -C 20 alkenyl, C 3 -C 8 haloalkenyl, C 5 -C 8 cycloalkenyl,
- C 3 -C 20 alkynyl optionally substituted with one phenyl group , C 3 -C 20 haloalkynyl , benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C 1 -C 4 alkyl, C ⁇ -C 4 haloalkyl,
- C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C j -C.haloalkyl,
- This invention also relates to compositions containing those compounds and methods for using those compounds and compositions.
- the compounds of the present invention, and compositions containing them are useful for the control of undesirable plant species.
- the compounds of the present invention are especially useful for the selective control of undesirable plant species in the presence of crops .
- the present invention provides a method for the control of undesirable plant species which comprises applying to the foliage of said plants or to the soil or water containing seeds or other propagating organs thereof, a herbicidally effective amount of a 3- (1,2- benzisothiazol- or isoxazol-5-yl) -2 , 4 (IH, 3H) -pyrimidine- dione or thione compound of formula I or a 3-(l,2-benz- isothiazol- or isoxazol-5-yl) -4 (3H) -pyrimidinone or thione compound of formula II.
- the herbicidal compounds of the present invention are represented by structural formulas I and II
- R, R x , R 2 , R 3 , A, A X , X, X x , Y and Z are as defined above for formulas I and II .
- formula I and II compounds of this invention are more effective and/or more selective herbicidal agents than the corresponding compounds exemplified in U.S. Patent Nos. 5,484,763 and 5,523,278 wherein Q is Q6.
- formula I compounds of the present invention are particularly useful for the selective control of undesirable plant species in the presence of crops such as corn, wheat, rice and soybeans.
- Preferred compounds of the present invention are those represented by structural formulas I and II
- R is C ⁇ -C 6 alkyl, C j -C j haloalkyl, C 3 -C 7 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, benzyl, 0R 4 or NR 5 R 6 ;
- R j and R 2 are each independently hydrogen, halogen, C j -C ⁇ l yl, C 3 -C 7 cycloalkyl, C.-C.haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, 0R 7 , S(0) n R 8 or NR 9 R 10 , and when R x and R 2 are taken together with the atoms to which they are attached, they represent a four- to seven- member ed saturated or unsaturated ring optionally interrupted by oxygen, sulfur or nitrogen, and optionally substituted with one to three methyl groups or one or more halogen atoms;
- R 3 is halogen or A 2 R U ;
- X is hydrogen, halogen or C 1 -C 4 alkyl;
- X x is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C ⁇ -C 4 alkoxy or C ⁇ -C 4 haloalkoxy ;
- Z is 0 or S(0) B ;
- Y is halogen, cyano, R 12 , X 2 R 12 , X 3 R 12 / X 2 X 3 ⁇ 2 or X 3 X 2 R i 2 ' X 2 is 0, S(0) p or NR 13 ;
- R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R n and R 14 are each independently hydrogen, C ⁇ C.-alkyl, C 3 -C 7 cycloalkyl, C 2 -C 6 alkenyl,
- R 12 is hydrogen , a C j -C 3 lkyl, C 3 -C 7 cycloalkyl, C 2 -C 6 alkenyl,
- N(R 29 )SO 2 R 30 group when R 12 and R 13 are taken together with the nitrogen atom to which they are attached, they form a 5- to 12-membered monocyclic or fused bicyclic, heterocyclic ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C 1 -C 4 alkyl, C 1 -C 4 halo- alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkyl- sulfonyl or X 4 R 22 groups;
- R 13 is hydrogen, C- ⁇ C ⁇ lkyl, C 3 -C 7 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, benzyl, OR 23 , cyano or S0 2 R S1 , and when R 13 and R 12 are taken together with the nitrogen atom to which they are attached,
- C(A 4 R 34 ) 2 , C(0)NR 35 R 36 , C(0)ON CR 37 R 3 ⁇ , C(0)NHOR 23 , cyano or 2-dioxolanyl group, or one phenyl, dihydrofuranone or furanone ring wherein each ring is optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C ⁇ -C 4 alkoxy groups or one to three C ⁇ -C 4 haloalkoxy groups, C 5 -C 8 cycloalkenyl optionally substituted with one C ⁇ -C 6 alkoxy, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C0 2 R 32 ,
- C(0)R 33 , C(A 4 R 34 ) 2 , C(0)NR 35 R 36 , C (0)ON CR 37 R 38 , C(0)NHOR 23 , cyano or 2-dioxolanyl group, or one phenyl, dihydrofuranone or furanone ring wherein each ring is optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C ⁇ -C 4 haloalkoxy groups, C 3 -C 10 alkynyl optionally substituted with one C ⁇ -C 6 alkoxy, C0 2 R 32 , C(0)R 33 , C(A 4 R 34 ) 2 , C(0)NR 35 R 36 ,
- C(0)ON CR 37 R 38 , C(0)NHOR 23 , cyano or 2-dioxolanyl group, or one phenyl, dihydrofuranone or furanone ring wherein each ring is optionally substituted with any combination of one to three halogen atoms, one to three C x -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups or one to three C 1 -C 4 haloalkoxy groups, phenyl optionally substituted with any combination of one to three halogen atoms, one to three
- C ⁇ -C 6 alkyl groups one to three C ⁇ -C 6 alkoxy groups, one C ⁇ -C 4 haloalkyl group, one C ⁇ -C 4 halo- alkoxy group, one -cyano group, one nitro group, one NR 39 R 40 group or one C(0)R 33 group, benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one to three C ⁇ -C 6 alkyl groups, one to three C ⁇ -C 6 alkoxy groups, one C ⁇ -C 4 haloalkyl group, one C ⁇ -C 4 haloalkoxy group, one cyano group, one nitro group, one NR 39 R 40 group or one C(0)R 33 group, or a 4- to 10-membered heterocyclic ring optionally substituted with any combination of one or two oxo groups , one or two thioxo groups , one to three halogen
- R x9 and R 26 are each independently hydrogen, C ⁇ -C 20 alkyl, C,-C 8 haloalkyl, C 3 -C 7 cycloalkyl, C 3 -C 7 halocycloalkyl, C 3 -C 20 alkenyl, C 3 -C 8 haloalkenyl, C 5 -C 8 cycloalkenyl, C 5 -C 8 halocycloalkenyl, C 3 -C 8 alkynyl, C 3 -C 8 haloalkynyl, Si(R 4X ) 3 , benzyl, phenyl,- furfuryl, pyridyl
- C ⁇ -C 20 alkyl optionally substituted with one C0 2 R 48 , C ⁇ -C 6 alkoxy or di(C ⁇ -C 4 alkyl) imino group,
- C 3 -C 20 haloalkynyl benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups, phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups, 2-, 3- or 4 -pyridyl, 2- or 3-furyl, 2- or 3 -thienyl, 2-tetrahydrofuranyl,
- R 34 , R 37 and R 38 are each independently C 1 -C 6 alkyl
- R 35 and R 49 are each independently hydrogen or C ⁇ -C 6 alkyl
- R 36 and R 50 are each independently hydrogen, cyano, C ⁇ -C 6 alkyl, S0 2 R sx or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C x -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups, or when R 35 and R 36 or R 49 and
- R 29 is hydrogen, C ⁇ -C 4 alkyl or C ⁇ -C 4 haloalkyl;
- R 24 , R 31 , R 4X and R 47 are each independently C ⁇ -C 4 alkyl, benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl,
- C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups;
- R 23 , R 39 , R 40 , R 42 , R 43 , R 44 , R 46 and R 48 are each independently hydrogen, C ⁇ -C 4 alkyl, benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl,
- C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C x -C 4 alkyl, C x -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups; and
- A, A x , A 2 , A 3 , A 4 , X 4 and X 5 are each independently O or S; and the optical isomers, diastereomers and/or tautomers thereof .
- R is C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl, C 3 -C 7 cycloa ⁇ lkyl,
- R x and R 2 are each independently hydrogen, halogen, C ⁇ -C 6 alkyl, C 3 -C 7 cycloalkyl, C j -C j haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, OR 7 , S(0) n R 8 or NR 9 R X0 , and when R x and R 2 are taken together with the atoms to which they are attached, they represent a four- to seven -membered saturated or unsaturated ring optionally interrupted by oxygen, sulfur or nitrogen, and optionally substituted with one to three methyl groups or one or more halogen atoms ;
- X is hydrogen, halogen or C ⁇ -C 4 alkyl;
- X ⁇ is hydrogen, halogen, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy or C ⁇ -C 4 haloalkoxy; Z is 0 or S(0) m ;
- Y is halogen, cyano, R x2 , X 2 R 12 ', X 3 R 12 , ⁇ 2 3 R 12 °r ⁇ 3 ⁇ 2 R l2 ;
- X 2 is 0, S(0) p or NR X3 ;
- R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R X4 are each independently hydrogen, C ⁇ -C 6 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 8 - alkoxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or benzyl;
- R 12 is hydrogen, a C ⁇ -C 8 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 8 alkenyl, C 5 -C 6 cycloalkenyl or C 2 -C 8 alkynyl group, wherein each group is optionally substituted with any combination of one to six halogen atoms, one to three C ⁇ -C 20 alkoxy groups
- R 22 and R 27 are each independently hydrogen, Si(R 31 ) 3 , C(0)NR 35 R 36 , C(0)R 33 , S0 2 R 47 ,
- C ⁇ -C 4 alkyl groups one to three C ⁇ -C 4 haloalkyl groups, one to three C ⁇ -C 4 alkoxy groups or one to three C ⁇ -C 4 haloalkoxy groups, or one 5- to 12-membered monocyclic or fused bicyclic, heterocyclic ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy, C ⁇ -C 4 haloalkoxy or C ⁇ -C 4 haloalkylsulfonyl groups, C 3 -C 20 alkenyl optionally substituted with one to three halogen atoms, one-- hydroxyl group, one C ⁇ -C 6 alkoxy, C0 2 R 32 , C(0)R 33 , C(A 4 R 34 ) 2 ,
- R X5 and R 20 are each independently hydrogen, a C j -C 8 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl group wherein each group is optionally substituted with one C0 2 R 42 group, benzyl optionally substituted with any combination of one to three halogen atoms, one to three C 1 -C 4 alkyl groups, one to three C ⁇ -C 4 haloalkyl groups, one to three C ⁇ -C 4 alkoxy groups or one to three C ⁇ -C 4 haloalkoxy groups, phenyl optionally substituted with any combination of one to three halogen atoms, one to three C ⁇ -C 4 alkyl groups, one to three C ⁇ -C 4 haloalkyl groups, one to three C ⁇ -C 4 alkoxy groups, one to three
- R X6 and R 2X are each independently hydrogen, C ⁇ -C 6 alkyl
- NR 46 R 48 , -N CR 46 R 4 ⁇ , C ⁇ -C 8 alkyl optionally substituted with one C ⁇ -C 6 alkoxy, thiophene or furan group, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl, C0 2 R 23 , C 2 -C 6 alkenyl optionally substituted with phenyl, benzyl optionally substituted with any combination of one to three halogen atoms, one to three C ⁇ -C 4 alkyl groups, one to three C ⁇ -C 4 haloalkyl groups, one to three C ⁇ -C 4 alkoxy groups, one to three C ⁇ -C 4 haloalkoxy groups, one nitro group, one cyano group or one X 4 R 22 group, phenyl optionally substituted with any combination of one to three halogen atoms, one to three C ⁇ -C 4 alkyl groups, one to three
- C j -C- ⁇ alkyl optionally substituted with one C0 2 R 48 , C ⁇ -C 6 alkoxy, C ⁇ -C 6 thioalkyl , C 2 -C 20 alkoxyalkoxy , phenyl, OSi(R 47 ) 3 , OC(0)R 33 , C 3 -C 7 cycloalkyl or di(C ⁇ -C 4 alkyl) imino group,
- C0 2 R 48 group C 3 - ⁇ C 8 halocycloalkyl, C 3 -C 20 alkenyl optionally substituted with one phenyl group , C 3 -C 15 haloalkenyl , C 5 -C 8 cycloalkenyl , C 5 -C 8 halocycloalkenyl , C 3 -C 20 alkynyl optionally substituted with one phenyl group , C 3 -C 20 haloalkynyl , benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C x -C 4 alkyl, C 1 -C 4 haloalkyl,
- C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C x -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups, 2-, 3- or 4 -pyridyl, 2- or 3-furyl, 2- or 3 -thienyl, 2-tetrahydrofuranyl, C ⁇ -C 4 alkyl substituted with one pyridyl, furyl, thienyl, tetrahydrofury1, C 3 -C 8 cycloalky1, dioxane or NR 49 R 50 group, or an alkali metal, alkaline earth metal, manganese, copper, zinc, cobalt, silver, nickel, ammonium or organic ammonium cation;
- R 34 , R 37 and R 38 are each independently C x -C 6 alkyl;
- R 35 and R 49 are each independently hydrogen or C ⁇ -C 6 alkyl and
- R 36 and R 50 are each independently hydrogen, cyano, C ⁇ -C 6 alkyl, S0 2 R 5X or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups, or when R 35 and R 36 or R 49 and R 50 are taken together with the nitrogen atom to which they are attached, they form a 5- to 12-membered monocyclic or fused bicyclic, heterocyclic ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C 1 -C 4 alkyl, C ⁇ -
- herbicidal agents of the present invention are those wherein
- R is C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl or benzyl;
- R x is halogen or C ⁇ -C 4 haloalkyl;
- R 2 is hydrogen, halogen or C x ⁇ C 4 haloalkyl; X and X ⁇ are each independently hydrogen or halogen; Z is O or S;
- Y is cyano, R 12 , X 2 R 12 or X 3 X 2 R 12 ;
- X 2 is 0, S or NR 13 ;
- R x2 is hydrogen, a C ⁇ -C 6 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 6 alkenyl,
- each group is optionally substituted with any combination of one to three halogen atoms, one or two C ⁇ -C 20 alkoxy groups, one or two C x -C 10 haloalkoxy groups, one NR 15 R 16 group, one S(0) q R x7 group, one or two cyano groups, one or two C(0)R X8 groups, one or two C0 2 R x9 groups, one or two C(0)SR X9 groups, one or two C(O)NR 20 R 2X groups, one or two X 4 R 22 groups, one P(0)(OR 23 ) 2 group, one Si(R 24 ) 3 group, one 4- to 10-membered monocyclic or fused bicyclic heterocyclic ring optionally substituted with any combination of one or two oxo groups , one or two thioxo groups , one to three halogen atoms, one to three C ⁇
- C ⁇ -C 4 alkoxy groups one to " three C ⁇ -C 4 haloalkoxy groups or one or two X 4 R 22 groups, one quaternary organic ammonium group, or one phenyl group optionally substituted with any combination of one to three halogen atoms, one C ⁇ -C 6 alkyl group, one C ⁇ -C 6 alkoxy group, one C 3 -C 7 cycloalkyl group, one cyano group, one nitro group, one C(0)R 25 group, one C0 2 R 26 group or one X 5 R 27 group, or phenyl optionally substituted with any combination of one or two halogen atoms , one to three C ⁇ -C 4 alkyl groups, one or two C ⁇ -C 4 alkoxy groups, one C 3 -C 6 cycloalkyl group, one C 1 -C 4 haloalkyl group, one C ⁇ -C 4 alkylthio group, one cyano
- R 28 is halogen
- R 22 and R 27 are each independently hydrogen, Si(R 3x ) 3 , C(0)NR 35 R 36 , C(0)R 33 , S0 2 R 47 ,
- C ⁇ -C 4 haloalkoxy groups or " one 5- to 12-membered monocyclic or fused bicyclic, heterocyclic ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy, C ⁇ -C 4 haloalkoxy or C ⁇ -C 4 haloalkylsulfonyl groups, C 3 -C 20 alkenyl optionally substituted with one to three halogen atoms, one hydroxyl group, one
- C(0)NR 35 R 36 , C(0)ON CR 37 R 38 , C (O) NR 35 OR 23 , cyano or 2-dioxolanyl group, or one phenyl, dihydrofuranone or furanone ring wherein each ring is optionally substituted with any combination of one to three halogen atoms, one to three C ⁇ -C 4 alkyl groups, one " to three C ⁇ -C 4 haloalkyl groups, one to three C ⁇ -C 4 alkoxy groups or one to three C ⁇ -C 4 haloalkoxy groups, phenyl optionally substituted with any combination of one to three halogen atoms, one to three
- C ⁇ -C 6 alkyl groups one to three C ⁇ -C 6 alkoxy groups, one C ⁇ -C 4 haloalkyl group, one C ⁇ -C 4 halo- alkoxy group, one cyano group, one nitro group, one NR 39 R 40 group or one C(0)R 33 group, benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one to three C ⁇ -C 6 alkyl groups, one to three C ⁇ -C 3 alkoxy groups, one C ⁇ -C 4 haloalkyl group, one C x -C 4 haloalkoxy group, one cyano group, one nitro group, one NR 39 R 40 group or one
- C(0)R 33 group or a 4- to 10-membered heterocyclic ring optionally substituted with any combination of one or two oxo groups , one or two thioxo groups , one to three halogen atoms, one to three C ⁇ -C 4 alkyl groups, one to three C ⁇ -C 4 haloalkyl groups, one to three C ⁇ -C 4 alkoxy groups or one to three C ⁇ -C 4 haloalkoxy groups;
- R 15 and R 20 are each independently hydrogen, a C ⁇ -C 6 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl group wherein each group is optionally substituted with one C0 2 R 42 group, benzyl optionally substituted with any combination of one to three halogen atoms , one to three C ⁇ -C 4 alkyl groups, one to three C ⁇ -C 4 halo
- R 16 and R 2X are each independently hydrogen, C ⁇ -C 6 alkyl
- R 17 , R X8 , R 25 , R 30 , R 33 , R 45 and R 5X are each independently
- NR 46 R 8 , -N CR 46 R 48 , C ⁇ -C 8 alkyl optionally substituted with one C ⁇ -C 6 alkoxy, thiophene or furan group,
- R 19 and R 26 are each independently hydrogen, C ⁇ -C 20 alkyl, C ⁇ -C 8 haloalkyl, C 3 -C 7 cycl
- C ⁇ -C 20 alkyl optionally substituted with one C0 2 R 48 , C ⁇ -C 6 alkoxy, C ⁇ -C 6 thioalkyl, C 2 -C 20 alkoxyalkoxy , phenyl, OSi(R 47 ) 3 , OC(0)R 33 , C 3 -C 7 cycloalkyl or di ( C x - C 4 alky 1 ) imino group ,
- C 0 2 R 8 group C 3 -C 8 halocycloalkyl , C 3 -C 20 alkenyl optionally substituted with one phenyl group, C 3 -C x5 haloalkenyl , C 5 -C 8 cycloalkenyl , C 3 -C 8 halocycloalkenyl , C 3 -C 20 alkynyl optionally substituted with one phenyl group , C 3 -C 20 haloalkynyl , benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl,
- C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C 1 -C 4 haloalkoxy groups,
- R 34 , R 37 and R 38 are each independently C j -C j alkyl;
- R 35 and R 49 are each independently hydrogen or C ⁇ -C 6 alkyl and
- R 36 and R 50 are each independently hydrogen, cyano, C 1 -C 6 alkyl, S0 2 R 51 or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇
- R 23 , R 39 , R 40 , R 42 , R 43 , R 44 , R 46 and R 48 are each independently hydrogen, C 2 -C 6 alkenyl, C 3 -C 8 cycloalkyl, C ⁇ -C a alkyl optionally substituted with one or two C ⁇ -C 4 alkoxy groups, benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C x -C 4 haloalkoxy groups, or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alk
- Another group of more preferred herbicidal agents of formula I are those wherein R is C ⁇ -C 4 alkyl; R x is C ⁇ -C 4 haloalkyl; R 2 is hydrogen,
- X and X x are each independently hydrogen or halogen; Z is 0 or S;
- R 12 is hydrogen, a C__-C 6 alkyl or C 2 -C 6 alkenyl group, wherein each group is optionally substituted with any combination of one to three halogen atoms, one or two C ⁇ -C 4 - alkoxy groups, one C ⁇ -C xo haloalkoxy group, one
- NR 15 R X6 group one S(0) q R 17 group, one or two cyano groups, one or two C(0)R x8 groups, one or two C0 2 R X9 groups, one or two C(O)NR 20 R 21 groups, one X 4 R 22 group, one P(0)(0R 23 ) 2 group, one 0C(0)R 33 group, one imidazole ring optionally substituted with any combination of one to three halogen atoms, one to three C ⁇ -C 4 alkyl groups, one to three C ⁇ -C 4 haloalkyl groups, one to three C ⁇ -C 4 alkoxy groups or one to three
- C x -C 4 haloalkoxy groups one phthalimide ring optionally substituted with any combination of one to three halogen atoms, one to three C ⁇ -C 4 alkyl groups, one to three C ⁇ -C 4 haloalkyl groups, one to three C ⁇ -C 4 alkoxy groups or one to three C ⁇ -C 4 haloalkoxy groups, one quaternary organic ammonium group, or one phenyl group optionally substituted with any combination of one to three halogen ato s, one C ⁇ -C 4 alkyl group, one C ⁇ -C 4 alkoxy group or one X 5 R 27 group, or phenyl optionally substituted with any combination of one or two halogen atoms, one to three C ⁇ -C 4 alkyl groups, one C ⁇ -C 4 alkoxy group, one
- R 13 is hydrogen, C ⁇ -C 6 alkoxyalkyl, C ⁇ -C 4 alkyl, 0R 23 , cyano or S0 2 R 51 ;
- R 28 is halogen
- R xs is hydrogen
- C ⁇ -C 4 alkyl optionally substituted with one C0 2 R 42 group
- benzyl optionally substituted with any combination of one to three halogen atoms, one to three
- R 16 is hydrogen, C ⁇ -C 4 alkyl, P(0)(0R 44 ) 2 , S0 2 R 45 , C(0)R 46 , or benzyl optionally substituted with any combination of one to three halogen atoms, one to three C ⁇ -C 4 alkyl groups, one to three C ⁇ -C 4 haloalkyl groups, one to three C ⁇ -C 4 alkoxy groups or one to three C ⁇ -C 4 haloalkoxy groups; R 2X is hydrogen, C ⁇ -C 6 alkyl, C ⁇ -C 4 alkoxy, C 3 -C 7 cycloalkyl, C 2 -C 6 alkenyl, C 3 -
- C ⁇ -C 4 alkyl groups one to three C 1 -C 4 haloalkyl groups, one to three C ⁇ -C 4 alkoxy groups -or one to three C ⁇ -C 4 haloalkoxy groups, or phenyl optionally substituted with any combination of one to three halogen atoms, one to three
- R 17 , R 18 , R 25 , R 30 , R 33 , R 45 and R 51 are each independently NR 46 R 48 , C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl,
- C 3 -C e alkynyl optionally substituted with one phenyl group , C 3 -C 6 haloalkynyl , benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups, phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups, C-C 4 alkyl substituted with one pyridyl, furyl, thienyl, tetrahydrofuryl or NR 49 R 50 group, or an alkali metal, alkaline earth metal, manga
- a third group of more preferred herbicidal agents of formula I are those wherein R is methyl; R x is trifluoromethyl;
- R 2 and X x are hydrogen
- X is hydrogen or fluorine
- Z is O or S
- Y is R 12 , C0 2 R X2 , C(0)R X2 or C(0)NR 3 R x2 ;
- R X2 is hydrogen
- C ⁇ -C 6 alkyl optionally substituted with any combination of one to three halogen atoms, one hydroxyl group, one or two C ⁇ -C 4 alkoxy groups, one C ⁇ -C 4 haloalkoxy group, one S0 2 R x7 group, one or two cyano groups, one C(0)R 18 group, one or two C0 2 R 19 groups, one or two C(O)NR 20 R 21 groups, one P(0)(OR 23 ) 2 group or one OC(0)R 33 group, C 2 -C 6 alkenyl optionally substituted with any combination of one C(0)R 18 group or one C0 2 R 19 group,
- R X3 is hydrogen, C ⁇ -C 4 alkyl or S0 2 R S1 ;
- R 14 is hydrogen, C ⁇ -C 4 alkyl or benzyl;
- R 18 , R 23 , R S6 and R 57 are each independently hydrogen or C 1 -C 3 alkyl
- R 52 , R 53 , R 54 and R S5 are each independently hydrogen
- R 19 is hydrogen, C ⁇ -C 4 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, benzyl, pyridyl or an alkali metal, alkaline earth metal, ammonium or organic ammonium cation;
- R 20 is hydrogen, a C ⁇ -C 6 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl group wherein each group is optionally substituted with one C0 2 R 42 group, benzyl optionally substituted with any combination of one to three halogen atoms, one to three C x -C 4 alkyl groups, one to three C ⁇ -C 4 halogen, provided that at least one of R 52 , R 53 , R 54 and R 55 is hydrogen ;
- R 19 is hydrogen, C ⁇ -C 4 alkyl, C 3 -C 6 alkenyl, C 3
- R 22 is hydrogen, C(0)R 33 , S0 2 R 47 , C ⁇ -C 4 alkyl optionally substituted with one cyano group ,
- R 32 is hydrogen , C ⁇ -C 4 alkyl optionally substituted with one C0 2 R 48 or
- C 3 -C G alkenyl optionally substituted with one phenyl group , C 3 -C 8 alkynyl optionally substituted with one phenyl group , C ⁇ -C 4 alkyl substituted with one pyridyl, furyl, thienyl, tetrahydrofuryl or NR 49 R 50 group, or an alkali metal, alkaline earth metal, ammonium or organic ammonium cation;
- R 35 and R 49 are each independently hydrogen or C 1 -C 4 alkyl
- R 36 is S0 2 R 51 or C ⁇ -C 3 alkoxy
- R x7 , R 33 and R 51 are each independently C ⁇ -C 4 alkyl
- R 26 is hydrogen, C ⁇ -C 4 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl,
- R 41 is C ⁇ -C 4 alkyl, benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C.alkyl, C ⁇ -C 4 haloalkyl , C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups, or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalk
- C ⁇ -C 4 alkoxy groups benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl,
- C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C 1 -C 4 alkyl, C ⁇ -C 4 haloalkyl, C 1 -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups; I is 0 or S;
- R 46 and R 48 are each independently hydrogen, C ⁇ -C 4 alkyl or benzyl ;
- R 47 is C ⁇ -C 4 alkyl;
- R so is C ⁇ -C 4 alkyl or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, C ⁇ -C 4 alkyl, C 1 -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups; and
- a and A x are O .
- Y is C ⁇ -C 3 alkyl, C0 2 R 32 , halomethyl , cyanomethyl,
- R 53 , R 54 , R 55 and R S6 are each independently hydrogen or methyl, provided that at least one of R 53 , R 54 and R 55 is hydrogen ;
- R 22 is cyanomethyl, methyl, ethyl, allyl or propargyl;
- R 32 is hydrogen,
- R 35 is hydrogen
- R 36 is S0 2 R 5X or C ⁇ -C 3 alkoxy
- R 17 and R 51 are each independently C-C 4 alkyl
- R 46 and R 48 are each independently hydrogen, C ⁇ -C 4 alkyl or benzyl; and A and A x are O.
- herbi ⁇ cidal agents include the group consisting of isopropyl ⁇ [ 2 - ⁇ 5- [3 , 6-dihydro-3-methyl-2 , 6-dioxo-4- (tri- fluoromethyl) -1(2H) -pyrimidinyl] -1, 2-benzisothiazol-
- halogen hereinabove are fluorine, chlorine, bromine and iodine.
- haloalkyl, halocycloalkyl, haloalkoxy, haloalkenyl, halocycloalkenyl and haloalkynyl designate an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, a cycloalkenyl group and an alkynyl group substituted with one or more halogen atoms , respectively.
- alkali metals include: sodium, potassium and lithium.
- Alkaline earth metals of formulas I and II include magnesium and calcium.
- organic ammonium is defined as a group consisting of a positively charged nitrogen atom joined to from one to four aliphatic groups, each containing from one to sixteen carbon atoms .
- 5- to 12-membered monocyclic or fused bicyclic, heterocyclic rings include, but are not limited to, benzimidazole, imidazole, imidazoline-2-thione, indole, isatoic anhydride, morpholine, piperazine, piperidine, purine, pyrazole, pyrrole, pyrrolidine and 1, 2, 4-triazole rings wherein each ring is optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy, C ⁇ -C 4 haloalkoxy or C ⁇ -C 4 haloalkylsulfonyl groups.
- 4 - to 10-membered heterocyclic rings include, but are not limited to, imidazole and phthalimide rings wherein each ring is optionally substituted with any combination of one to three halogen atoms, one to three C x -C 4 alkyl groups, one to three C ⁇ -C 4 haloalkyl groups, one to three C x -C 4 alkoxy groups, one to three C ⁇ -C 4 haloalkoxy groups or one or two X 4 R 22 groups.
- the formula I and II compounds of the present invention are effective herbicidal agents useful for the control of a wide variety of undesirable plant species. Those compounds are effective for controlling weeds native to both dry land and wet land areas . The compounds are effective in controlling the above-said plants when applied to the foliage thereof or to the soil or water containing seeds or other propagating organs thereof such as stolons, tubers or rhizomes, at rates of from about 0.001 kg/ha to 4 kg/ha and preferably from about 0.001 kg/ha to 1 kg/ha.
- the formula I and II compounds of this invention are particularly useful for the selective control of undesirable plant species in the presence of crop plants, crop seeds or other crop propagating organs.
- some of the compounds of this invention are selective in soybeans and/or cereal crops such as corn, wheat and rice when applied as preemergence and/or postemergence treatments .
- the formula I and II compounds of this invention may be used for the selective control of undesirable plant species in transplanted rice culture by applying a herbicidally effective amount of a formula I compound to the soil or water containing seeds or other propagating organs of said undesirable plant species after the rice has been transplanted.
- Formula I compounds of this invention which are especially useful for the selective control of undesirable plant species in the presence of corn include isopropyl ⁇ ⁇ 2- ⁇ 5- [3, 6 -dihydro-3 -methyl-2 , 6-dioxo-4- (tri- fluoromethyl ) -1(2H) -pyrimidinyl] -1, 2-benzisothiazol- 3-yl] -p-tolyl ⁇ oxy]acetate; methyl " f ⁇ 2- ⁇ 5- [3, 6-dihydro-3-methyl-4- (trifluoromethyl) - 2, 6-dioxo-l(2H) -pyrimidinyl] -1, 2-benzisothiazol-3- yl ⁇ -p-tolyl ⁇ oxy ⁇ acetate; 2-(dimethylamino)ethyl ⁇ ⁇ 2- ⁇ 5- [3, 6 -dihydro-3 -methyl-2, 6- dioxo-4- (trifluoromethyl) -1(2H) -pyr
- Formula I compounds of the present invention which are particularly useful for the selective control of undesirable plant species in the presence of wheat include isopropyl ⁇ ⁇ 2- ⁇ 5- [3, 6-dihydro-3-methyl-2, 6-dioxo-4- (tri- fluoromethyl ) -1 ( 2H) -pyrimidinyl] -1, 2-benzisothiazol-
- Formula I compounds of this invention which are particularly useful for the selective control of undesirable plant species in the presence of soybeans include methyl 2- ⁇ ⁇ 2- ⁇ 5- [3, 6-dihydro- 3 -methyl-4- (trifluoromethyl) -2, 6 -dioxo-1(2H>--pyrimidinyl] -1, 2- enz- isothiazol-3-yl ⁇ -p-tolyl ⁇ oxy ⁇ propionate; methyl 2- ⁇ ⁇ 6- ⁇ 5- [3, 6 -dihydro- 3 -methyl-4- (trifluoro- methyl) -2, 6-dioxo-l(2H) -pyrimidinyl] -1, 2 -benz- isothiazol-3-yl ⁇ -3,4 -xylyl ⁇ oxy ⁇ propionate; l-methyl-3- (3-methyl-l, 2-benzisothiazol-5-yl) -6- (tri- fluoromethyl ) -2, 4 (IH, 3H) -
- While the compounds of this invention are effective for controlling undesirable plant species when employed alone, they may also be used in combination with other biological chemicals, including herbicides.
- the compounds of this invention may be applied to the foliage of undesirable plant species or to the soil or water containing seeds or other propagating organs thereof in the form of a solid or liquid herbicidal composition, comprising a herbicidally effective amount of the desired compound dispersed or dissolved in an agronomically acceptable, inert solid or liquid carrier.
- the compositions may be applied as preemergence or postemergence treatments .
- the formula I and II compounds of the present invention may be formulated as emulsifiable concentrates, wettable powders, granular formulations, suspension concentrates, flowable concentrates and the like.
- Formula I compounds wherein Z is S may be prepared, as illustrated in Flow Diagram I, by cyclizing a ketone of formula III with sulfur and ammonium hydroxide or ammonia to form a nitrobenzisothiazole of formula IV, reducing the formula IV compounds using conventional reducing agents such as an iron in acetic acid to form an aminobenzisothiazole of formula V, reacting the formula V compound with phosgene or a phosgene equivalent to form an isocyanate of formula VI, reacting the isocyanate with a 3-aminoacrylate of formula VII in the presence of a base such as sodium hydride to form an intermediate compound of formula VIII, and reacting the formula VIII compound with an electrophile of formula IX in the presence of a base such as potassium carbonate.
- a base such as sodium hydride
- Formula I compounds wherein Z is S may also be prepared, as shown in Flow Diagram II, by reacting an aminobenzisothiazole of formula V with a 1, 3-propanedione of formula X in the presence of a base such as triethylamine to form an intermediate compound of formula XI , and reacting the formula XI compound with phosgene or thiophosgene or an equivalent thereof followed by an amine of formula XII in the presence of a base such as triethylamine or pyridine.
- a base such as triethylamine
- formula I compounds wherein Z is S may be prepared, as shown in Flow Diagram III, by reacting an aminobenzisothiazole of formula V with a 2 - dialkylamino-6H-l, 3-oxazin-6-one of formula XIII in the presence of an organic acid such as acetic acid to form an intermediate compound of formula VIII, and reacting the formula VIII compound with an electrophile of formula IX in the presence of a base such as potassium carbonate.
- a base such as potassium carbonate
- Formula I compounds wherein Z is O may be prepared, as shown in Flow Diagram IV, by reacting a ketone of formula III with hydroxylamine hydrochloride optionally in the presence of sodium acetate to form an oxime of formula XIV, cyclizing the formula XIV compound with a base such as potassium hydroxide to form a nitrobenz- isoxazole of formula XV, reducing the formula XV compound using conventional reducing agents such as tin(II) chloride in acetic acid to form an aminobenzisoxazole of formula XVI, reacting the formula XVI compound with a 2-dialkylamino-6H-l, 3-oxazin-6-one of formula XIII in the presence of an organic acid such as acetic acid to form an intermediate compound of formula XVII, and reacting the formula XVII compound with an electrophile of formula IX in the presence of a base such as potassium carbonate.
- a base such as potassium carbonate
- nitrobenzisoxazole compounds of formula XV may be prepared, as shown in Flow Diagram V, by reacting a ketone of formula XVIII with hydroxylamine hydrochloride optionally in the presence of a base such as sodium acetate to form an oxime of formula XIX, cyclizing the formula XIX compound with 1, 1' -carbonyldi- imidazole in the presence of a base such as triethylamine to form a benzisoxazole of formula XX, and nitrating the formula XX compound using conventional methods such as a nitric acid/sulfuric acid mixture.
- Formula I compounds wherein Y is halomethyl may be prepared, as shown in Flow Diagram VI, by halogenating a formula I compound wherein Y is methyl with a halogenating agent such as N-bromosuccinimide, N-chlorosuccin- imide, N-iodosuccinimide, bromine, chlorine, sulfuryl chloride, sulfuryl bromide and the like.
- a halogenating agent such as N-bromosuccinimide, N-chlorosuccin- imide, N-iodosuccinimide, bromine, chlorine, sulfuryl chloride, sulfuryl bromide and the like.
- Formula I compounds wherein Y is a C ⁇ -C 20 alkoxymethyl group may be prepared, as shown in Flow Diagram VII, by reacting a formula I compound wherein Y is bromomethyl with a C ⁇ -C 20 alcohol in the presence of silver trifluoromethanesulfonate.
- Formula I compounds wherein Y is methyl substituted with one X 4 R 22 group may be prepared, as shown in Flow Diagram VIII, by reacting a formula I compound wherein Y is bromomethyl with an alcohol or thiol of formula XXI in the presence of a base such as sodium hydride.
- Formula I compounds wherein Y is C ⁇ -C 4 alkylthiomethyl may be prepared, as shown in Flow Diagram IX, by reacting a formula I compound wherein Y is bromomethyl with an alkali metal thioalkoxide.
- Formula V intermediate compounds wherein Y is OR 12 may be prepared, as shown in Flow Diagram X, by nitrating a benzisoxazol-3-ol or benzisothiazol-3-ol of formula XXII with a conventional nitrating agent such as a nitric acid/sulfuric acid mixture to form a 5-nitrobenzisoxazol- 3-ol or 5-nitrobenzisothiazol-3-ol of formula XXIII, reacting the formula XXIII compound with an electrophile of formula XXIV in the presence of a base such as potassium carbonate to form an intermediate compound of formula XXV, and reducing the formula XXV compound using conventional reducing agents .
- Formula V intermediate compounds wherein Y is Cl or Br may be prepared, as shown in Flow Diagram XI, by reacting a 5-nitrobenzisoxazol-3-ol or 5-nitrobenziso- thiazol-3-ol of formula XXIII with phosphorous oxychlor- ide, phosphorous oxybromide or phosphorous pentabromide to form a 3-halo-5-nitrobenzisoxazol or 3-halo-5-nitro- benzisothiazol of formula XXVI, and reducing the formula XXVI compound using conventional reducing agents.
- Formula I compounds wherein A is 0 and A x is S may be prepared, as shown in Flow Diagram XII, by reacting a formula I compound wherein A and A x are O with Lawesson's Reagent (2, 4-bis(4-methoxyphenyl) -1, 3-dithia-2,4-diphos- phetane-2,4-disulfide) in the presence of a base such as sodium hydrogen carbonate.
- Lawesson's Reagent 4-bis(4-methoxyphenyl) -1, 3-dithia-2,4-diphos- phetane-2,4-disulfide
- Formula I compounds wherein A and A x are S may be prepared, as shown in Flow Diagram XIII, by reacting a formula I compound wherein A is S and A x is 0 with Lawesson's Reagent in the presence of a base. FLOW DIAGRAM XIII
- Formula I compounds wherein R 19 , R 26 and R 32 are hydrogen may be prepared by hydrolyzing a corresponding formula I ester with an acid such as trifluoroacetic acid.
- the resultant formula I acid may then be reacted with thionyl chloride or oxalyl chloride to form an acid chloride which is then reacted with an R 19 OH, R 26 OH or R 32 OH alcohol or an HNR 20 R 21 , HNR 3S R 36 or HNR 49 R 50 amine to form additional compounds of formula I .
- Formula I compounds wherein R 19 , R 26 and R 32 are an alkali metal, alkaline earth metal, manganese, copper, zinc, cobalt, silver, nickel, ammonium or organic ammonium cation may be prepared from formula I compounds wherein R X9 , R 26 and R 32 are hydrogen using conventional methods .
- Intermediate compounds of formula IV wherein Y is alkyl substituted with one C0 2 R 19 group may be prepared, as shown in Flow Diagram XIV, by reacting an intermediate compound of formula XXVI with an oxylate of formula XXVII in the presence of a base to form an intermediate compound, reacting the intermediate compound with urea to ⁇ form a compound of formula XXVIII wherein Y is methyl substituted with one C0 2 R 19 group, and optionally reacting the formula XXVIII compound with a C ⁇ -C 5 alkyl halide in the presence of a base such as sodium hydride to form a compound of formula XXIX.
- the formula XXVIII and XXIX compounds may be saponified to form compounds wherein R 19 is hydrogen .
- formula III compounds wherein Y is an ⁇ -methylacetate group may be prepared as shown in Flow Diagram XV. FLOW DIAGRAM XV
- Intermediate compounds of formula III wherein Y is methyl substituted with one C0 2 R 19 group may be prepared by reacting an acid chloride of formula XXX with an acetate of formula XXXI in the presence of a base such as sodium hydride, and optionally reacting the formula III compound wherein Y is methyl substituted with one C0 2 R 19 group with a C ⁇ -C 5 alkyl halide in the presence of a base such as sodium hydride to form a formula III compound wherein Y is an ⁇ -alkylacetate group.
- the reactions are shown below in Flow Diagram XVI . FLOW DIAGRAM XVI
- Formula IV and XV compounds wherein Y is an alkyl or phenyl group substituted with one C(0)R 18 or C(0)R 2S group may be prepared by reacting the corresponding acid chloride with an appropriately substituted magnesium bromide compound, copper bromide compound or lithium compound.
- the reaction scheme is exemplified below for the case where Y is phenyl substituted with one C(0)R 25 group.
- Formula I, IV and XV compounds wherein Y is alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl or phenyl substituted with a CHO group may be prepared by reducing a formula I, IV or XV compound wherein Y is alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl or phenyl substituted with a C0 2 H group with a conventional reducing agent such as a borane-tetrahydrofuran complex to form a formula I, IV or XV compound wherein Y is alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl or phenyl substituted with a CH 2 OH group, and oxidizing the resultant alcohol with a conventional oxidizing agent such as chromium(VI) oxide.
- a conventional oxidizing agent such as chromium(VI) oxide
- Formula IV an XV compounds wherein Y is alkyl or cycloalkyl substituted with a C(0)R 18 group may be prepared by reacting a formula IV or XV compound wherein Y is haloalkyl or halocycloalkyl with a lithium reagent of formula XXXII to form an intermediate compound, and reacting the intermediate compound with a Lewis Acid such as borontrifluoride in the presence of water.
- a Lewis Acid such as borontrifluoride
- Formula I compounds wherein Y is formyl may also be prepared as shown in Flow Diagram XX. FLOW DIAGRAM XX
- Formula IV an XV compounds wherein Y is X 2 R 12 and R 12 is optionally substituted phenyl may be prepared, as shown in Flow Diagram XXI , by reacting a formula IV or XV compound wherein Y is Br with an R l2 X 2 H compound in the presence of a base such as potassium carbonate.
- Formula IV and XV compounds wherein Y is trifluoro- methyl may be prepared, as shown in Flow Diagram XXII, by reacting a formula IV or XV compound wherein Y is Br with a silyl compound of formula XXXIII in the presence of copper(I) iodide and potassium iodide.
- formula III and XIV compounds wherein Y is trifluoromethyl may be prepared by reacting a formula IV or XV compound wherein Y is Br with sodium trifluoroacetate in the presence of a catalyst such as a tetrasubstituted palladium catalyst.
- a catalyst such as a tetrasubstituted palladium catalyst.
- Formula I compounds wherein Y is CH 2 CN may be prepared, as shown in Flow Diagram XXIV, by reacting a formula I compound wherein Y is CH 2 Br with potassium cyanide.
- Formula I compounds wherein Y is R X2 or X 2 R 12 and R 12 is chloroalkyl, fluoroalkyl or iodoalkyl may be prepared by reacting the corresponding formula I compound wherein R 12 is bromoalkyl with lithium chloride, sodium iodide, potassium fluoride or silver (I) fluoride.
- the reaction scheme is exemplified below in Flow Diagram XXV for the case where Y is fluoromethyl, iodomethyl and chloro- methyl .
- Formula I compounds wherein A is S and A x is O may be prepared, as shown in Flow Diagram XXVI, by reacting an amine of formula V or XVI with thiophosgene or a thiophosgene equivalent in the presence of a base such as triethylamine to form an isothiocyanate of formula XXXIV, and reacting the formula XXXIV compound with an alkene of formula XXXV in the presence of a base such as sodium hydride .
- a base such as sodium hydride
- Formula I compounds wherein A and A x are O may be prepared, as shown in Flow Diagram XXVII, by reacting an isocyanate of formula XXXVI with an alkene of formula
- Intermediate compounds of formula III wherein Y is acetate substituted with ⁇ - (C x -C 6 alkyl) or ⁇ , ⁇ -bis(C x -C 6 - alkyl) may be prepared by treated an acid chloride of formula XLI with zinc and an ⁇ -halo ester of formula XLII to form an intermediate keto-ester of formula XLIII, which is nitrated to form an intermediate of formula III .
- the reaction scheme is shown in Flow Diagram XXVIII. FLOW DIAGRAM XXVIII
- Formula V intermediate compounds wherein Y is Cl or Br may also be prepared, as shown in Flow Diagram XXIX, by reacting a 5-nitrobenzisothiazole or 5-nitrobenziso- xazole of formula XLIV with chlorine or bromine in an acid such as acetic acid.
- the reaction scheme is shown below in Flow Diagram XXIX. FLOW DIAGRAM XXIX
- Formula I compounds wherein Y is C(0)X 2 R 12 and X 2 is O may be prepared as shown in Flow Diagram XXX.
- Formula I compounds wherein Y is C (0) NR X2 R x3 may be prepared as shown below in Flow Diagram XXXI .
- Formula I compounds wherein Y is C(O)NR 13 S0 2 NR 46 R 4B may be prepared as shown below in Flow Diagram XXXII.
- Formula I compounds wherein Y is C(0)N(R x2 )OR 23 may be prepared as shown in Flow Diagram XXXIV.
- Formula I compounds wherein Y is CH(0H)R 23 , C(0)R 23 , CH(OR 22 )R 23 and CH(R 23 )0C(0)R 33 may be prepared as shown below in Flow Diagram XXXV.
- the present invention also relates to intermediate compounds having the structural formula XLV
- R x , R 2 , A, A ⁇ / X, X x , Y and Z are as described hereinabove for formula I .
- Preferred intermediate compounds of formula XLV are those wherein
- R x and R 2 are each independently hydrogen, halogen, C ⁇ -C 6 alkyl, C 3 -C 7 cycloalkyl, C ⁇ -C ⁇ haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, OR 7 , S(0) 0 R 8 or NR 9 R 10 , and when R x and R 2 are taken together with the atoms to which they are attached, they represent a four- to seven-membered saturated or unsaturated ring optionally interrupted by oxygen, sulfur or nitrogen, and optionally substituted with one to three methyl groups or one or more halogen atoms;
- X is hydrogen, halogen or C ⁇ -C 4 alkyl;
- X ⁇ is hydrogen, halogen, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy or
- Y is halogen, cyano, R 12 , X 2 R X2 , X 3 R 12 , X 2 X 3 R 12 or X 3 X 2 R X2 ;
- X 2 is 0, S(0) p or NR 3 ;
- R 4 , R s , R 6 , R 7 , R 8 , R 9 , R x0 and R X4 are each independently hydrogen, C ⁇ -C 6 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 6 alkenyl,
- R X2 is hydrogen , a C ⁇ -C 6 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 6 alkenyl,
- each group is optionally substituted with any combination of one to six halogen atoms, one to three C ⁇ -C 20 alkoxy groups, one or two C x -C xo haloalkoxy groups, one or two NR 15 R xe groups, one to three S(0) q R 17 groups, one or two cyano groups, one or two C(0)R x8 groups, one or two
- C0 2 R 19 groups one or two C(O)NR 20 R 2X groups, one to three X 4 R 22 groups, one or two P(0)(OR 23 ) 2 groups, one or two Si(R 24 ) 3 groups, one 4- to 10-membered heterocyclic ring optionally substituted with any combination of one or two oxo groups, one or two thioxo groups, one to three halogen atoms, one to three C x -C 4 alkyl groups, one to three C ⁇ -C 4 haloalkyl groups, one to three C ⁇ -C 4 alkoxy groups, one to three
- C x -C 4 haloalkyl groups one to three C x -C 4 alkoxy groups or one to three C ⁇ -C 4 haloalkoxy groups, or one 5- to 12-membered monocyclic or fused bicyclic, heterocyclic ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C ⁇ -C 4 alkyl, C x -Chaloalkyl, C ⁇ -C 4 alkoxy, C ⁇ -C 4 haloalkoxy or C x -C 4 haloalkylsulfonyl groups,
- C 3 -C 20 alkenyl optionally substituted with one to three halogen atoms, one C ⁇ -C 6 alkoxy, C0 2 R 32 , C(0)R 33 , C(A 4 R 34 ) 2 , C(0)NR 35 R 36 , C(0)ON CR 37 R 38 , C(0)NHOR 23 , cyano or 2-dioxolanyl group, or one phenyl, dihydrofuranone or furanone ring wherein each ring is optionally substituted with any combination of one to three halogen atoms, one to three C ⁇ -C 4 alkyl groups, one to three C ⁇ -C 4 haloalkyl groups, one to three C x -C 4 alkoxy groups or one to three C ⁇ -C 4 haloalkoxy groups,
- R 16 and R 2X are each independently hydrogen, C ⁇ -C 6 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 6 alkenyl, C 3 -C 7 cycloalkenyl, C 2 -C 6 alkynyl, P(0)(OR 44 ) 2 , S0 2 R 45 , C(0)R 46 , benzyl optionally substituted with any combination of one to three halogen atoms, one to three
- R x7 , R x8 , R 25 , R 30 , R 33 , R 45 and R 5X are each independently C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C0 2 R 23 , C 2 -C 6 alkenyl optionally substituted with phenyl
- R X9 and R 26 are each independently hydrogen, C x -C 20 alkyl, C ⁇ -C 8 haloalkyl, C 3
- C ⁇ -C 20 alkyl optionally substituted with one C0 2 R 48 , C ⁇ -C 6 alkoxy or di ( C ⁇ -C 4 alkyl ) imino group , C ⁇ -C ls haloalkyl ,
- R 34 , R 37 and R 38 are each independently C ⁇ -C 6 alkyl;
- R 35 and R 49 are each independently hydrogen or C ⁇ -C 6 alkyl and
- R 36 and R 50 are each independently hydrogen, cyano, C x -C 6 alkyl, S0 2 R 5x or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -Calkoxy and C ⁇ -C 4 haloalkoxy groups, or when R 35 and R 36 or R 49 and R so are taken together
- R 24 , R 3X , R 4X and R 47 are each independently C x -C 4 alkyl, benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C x -C 4 alkyl, C x -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups, or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C x -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups;
- R 23 , R 39 , R 40 , R 42 , R 43 , R 44 , R 46 and R 48 are each independently hydrogen, C ⁇ -C 4 alkyl, benzyl optionally substituted with one or more groups independently selected from halogen,
- R x and R 2 are each independently hydrogen, halogen, C ⁇ -C 6 alkyl, C 3 -C 7 cycloalkyl, C ⁇ -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, OR 7 , S(0) n R 8 or NR 9 R X0 , and when R x and R 2 are taken together with the atoms to which they are attached, they represent a four- to seven-membered saturated or unsaturated ring optionally interrupted by oxygen, sulfur or nitrogen, and optionally substituted with one to three methyl groups or one or more halogen atoms ;
- X is hydrogen, halogen or C ⁇ -C 4 alkyl;
- X ⁇ is hydrogen, halogen, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl,
- Y is halogen, cyano, R X2 , X 2 R 12 , X 3 R l2 , X 2 X 3 ⁇ 2 or X 3 X 2 R 12 ;
- X 2 is 0, S(0) p or NR 13 ;
- R 4 , R s , R 6 , R 7 , R 8 , R 9 , R 10 and R X4 are each independently hydrogen, C ⁇ -C 6 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 8 - alkoxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or benzyl;
- R x2 is hydrogen, a C ⁇ -C 8 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 8 alkenyl,
- each group is optionally substituted with any combination of one to six halogen atoms, one to three C x -C 20 alkoxy groups optionally substituted with one C ⁇ -C 6 alkoxy, benzyloxy or C ⁇ -C 6 alkylthio group, one or two C ⁇ -C xo haloalkoxy groups, one or two NR X5 R 16 groups, one to three S(0) q R x7 groups, one or two cyano groups, one or two C 3 -C 7 cycloalkyl groups, one thiocyano group, one
- C ⁇ -C 6 alkyl groups one to three C ⁇ -C 3 alkoxy groups, one C 3 -C 7 cycloalkyl group, one C x -C 4 haloalkyl group, one C ⁇ -C 4 alkylthio group, one cyano group, one nitro group, one C(0)R 25 group, one C0 2 R 26 group or one
- X 5 R 27 group phenyl optionally substituted with any combination of one to three halogen atoms, one to three C x -C 4 alkyl groups, one to three C x -C 4 alkoxy groups, one C 3 -C 6 cycloalkyl group, one
- heterocyclic ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C ⁇ -C 4 alkyl, C ⁇ -C 4 halo- alkyl, C ⁇ -C 4 alkoxy, C ⁇ -C 4 haloalkoxy, C ⁇ -C 4 haloalkyl- sulfonyl or X 4 R 22 groups;
- R x3 is hydrogen, C x -C 8 alkoxyalkyl, C x -C 6 alkyl,
- R 22 and R 27 are each independently hydrogen, Si(R 31 ) 3 , C(0)NR 3S R 36 , C(0)R 33 , S0 2 R 47/
- R X6 and R 2X are each independently hydrogen, C ⁇ -C 6 alkyl
- NR 46 R 48 , -N CR 46 R 48 , C ⁇ -C 8 alkyl optionally substituted with one C ⁇ -C 6 alkoxy, thiophene or furan group, C ⁇ -C 6 haloalkyl, C 3 -C 8 cycloalkyl, C0 2 R 23 , C 2 -C 6 alkenyl optionally substituted with phenyl, benzyl optionally substituted with any combination of one to three halogen atoms, one to three C ⁇ -C 4 alkyl groups, one to three C ⁇ -C 4 haloalkyl groups, one to three C ⁇ -C 4 alkoxy groups, one to three C x -C 4 haloalkoxy groups, one nitro group, one cyano group or one X 4 R 22 group, phenyl optionally substituted with any combination of one to three halogen atoms, one to three C ⁇ -C 4 alkyl groups, one to three
- R x9 and R 26 are each independently hydrogen, C 1 -C 20 alkyl, C ⁇ -C 8 haloalkyl, C 3 -C 7 cycloalkyl, C 3 -C 7 halocycloalkyl, C 3 -C 20 alkenyl, C 3 -C 8 haloalkenyl, C 5 -C 8 cycloalkenyl, C 5 -C 8 halocycloalkenyl, C 3 -C 8 alkynyl, C 3 -C 8 haloalkynyl, Si(R 4X ) 3 , benzyl, phenyl, furfuryl, pyridyl, thienyl, oxi ino or an alkali metal, alkaline earth metal, manganese, copper, zinc, cobalt, silver, nickel, ammonium or organic ammonium cation; R 32 is hydrogen, Si(R 47 ) 3 , di(C ⁇ -C 4 alky
- C x -C 20 alkyl optionally substituted with one C0 2 R 48 , C ⁇ -C 6 alkoxy , C ⁇ -C 6 thioalkyl , C 2 -C 20 alkoxyalkoxy , phenyl , OSi (R 47 ) 3 , OC ( 0) R 33 , C 3 -C 7 cycloalkyl or di (C ⁇ -C 4 alkyl ) imino group ,
- C0 2 R 48 group C 3 -C 3 halocycloalkyl , C 3 -C 20 alkenyl optionally substituted with one phenyl group , C 3 -C X5 haloalkenyl , C 5 -C 8 cycloalkenyl , C 5 -C 8 halocycloalkenyl , C 3 -C 20 alkynyl optionally substituted with one phenyl group , C 3 -C 20 haloalkyny1 , benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups, phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇
- R 34 , R 37 and R 38 are each independently C ⁇ -C 6 alkyl;
- R 35 and R 49 are each independently hydrogen or C ⁇ -C 6 alkyl and
- R 36 and R 50 are each independently hydrogen, cyano, C ⁇ -C 6 alkyl, S0 2 R 5X or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇
- R 24 , R 3X , R 4X and R 47 are each independently C ⁇ -C 4 alkyl, benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C x -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups, or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups;
- R 23 , R 39 , R 40 , R 42 , R 43 , R 44 , R 46 and R 48 are each independently hydrogen, C 2 -C 6 alkenyl, C 3 -C 8 cycloalkyl, C x -C 8 al
- C ⁇ -C 4 alkoxy groups benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups, or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl,
- R 46 and R 48 when R 46 and R 48 are taken together with the atom to which they are attached, they form a 5- to 12- membered monocyclic or fused bicyclic, heterocyclic or cycloalkyl ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C ⁇ -C 4 alkyl, C x -C 4 haloalkyl, C ⁇ -C 4 alkoxy, C ⁇ -C 4 haloalkoxy or C ⁇ -C 4 haloalkylsulfonyl groups; and A, A x , A 3 , A 4 , X 4 and X 5 are each independently 0 or S; and the optical isomers, diastereomers and/or tautomers thereof .
- More preferred formula XLV intermediate compounds of this invention are those wherein R x is halogen or C ⁇ -C 4 haloalkyl; R 2 is hydrogen, halogen or C ⁇ -C 4 haloalkyl; X and X x are each independently hydrogen or halogen; Z is 0 or S; Y is cyano, R 12 , X 2 R X2 or X 3 X 2 R X2 ; X. is O, S or NR X3 ;
- R x2 is hydrogen, a C ⁇ -C 6 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 6 alkenyl , C 5 -C 6 cycloalkenyl or C 2 -C 6 alkynyl group, wherein each group is optionally substituted with any combination of one to three halogen atoms , one or two C ⁇ -C 20 alkoxy groups, one or two C ⁇ -C o haloalkoxy groups, one NR X5 R X6 group, one S(0) q R 17 group, one or two cyano groups, one or two C(0)R X8 groups, one or two C0 2 R 19 groups, one or two C(0)SR x9 groups, one or two C(O)NR 20 R 2X groups, one or
- C ⁇ -C 4 haloalkyl groups one to three C ⁇ -C 4 alkoxy groups, one to three C ⁇ -C 4 haloalkoxy groups or one or two X 4 R 22 groups, one quaternary organic ammonium group, or one phenyl group optionally substituted with any combination of one to three halogen atoms, one C x -C 6 alkyl group, one C ⁇ -C 6 alkoxy group, one C 3 -C 7 cycloalkyl group, one cyano group, one nitro group, one C(0)R 25 group, one C0 2 R 26 group or one X 5 R 27 group, or phenyl optionally substituted with any combination of one or two halogen atoms , one to three C ⁇ -C 4 alkyl groups, one or two C ⁇ -C 4 alkoxy groups, one C 3 -C 6 cycloalkyl group, one C ⁇ -C 4 haloalkyl group, one
- R X3 is hydrogen, C 2 -C 6 alkoxyalkyl, C ⁇ -C 4 alkyl, C 3 -C 7 cyclo- alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, benzyl, OR 23 , cyano or S0 2 R 51 ;
- R 28 is halogen;
- R 22 and R 27 are each independently hydrogen, Si(R 3x ) 3 , C(0)NR 35 R 36 , C(0)R 33 , S0 2 R 47 ,
- C ⁇ -C 4 alkyl groups one to three C ⁇ -C 4 haloalkyl groups, one to three C ⁇ -C 4 alkoxy groups or one to three C ⁇ -C 4 haloalkoxy groups, or one 5- to 12-membered monocyclic or fused bicyclic, heterocyclic ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C ⁇ -C 4 alkyl,
- C(0)NR 3S R 36 , C (O)ON CR 37 R 38 , C (O) NR 35 OR 23 , cyano or 2-dioxolanyl group, or one phenyl, dihydrofuranone or furanone ring wherein each ring is optionally substituted with any combination of one to three halogen atoms, one to three C ⁇ -Calkyl groups, one to three C ⁇ -C 4 haloalkyl groups, one to three C ⁇ -C 4 alkoxy groups or one to three C ⁇ -C 4 haloalkoxy groups, phenyl optionally substituted with any combination of one to three halogen atoms, one to three
- C ⁇ -C 6 alkyl groups one to three C ⁇ -C 6 alkoxy groups, one C ⁇ -C 4 haloalkyl group, one C ⁇ -C 4 halo- alkoxy group, one cyano group, one nitro group, one NR 39 R 40 group or one C(0)R 33 group, benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one to three C ⁇ -C 6 alkyl groups, one to three C ⁇ -C 6 alkoxy groups, one C x -C 4 haloalkyl group, one C x -C 4 haloalkoxy group, one cyano group, one nitro group, one NR 39 R 40 group or one
- C(0)R 33 group or a 4- to 10-membered heterocyclic ring optionally substituted with any combination of one or two oxo groups, one or two thioxo groups, one to three halogen atoms, one to three C ⁇ -C 4 alkyl groups, one to three C x -C 4 haloalkyl groups, one to three C ⁇ -C 4 alkoxy groups or one to three C ⁇ -C 4 haloalkoxy groups;
- d R 20 are each independently hydrogen, a C ⁇ -C 6 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl group wherein each group is optionally substituted with one C0 2 R 42 group, benzyl optionally substituted with any combination of one to three halogen atoms , one to three C ⁇ -C 4 alkyl groups, one to three C x -C 4 haloalkyl
- NR 46 R 48 , -N CR 46 R 48 , C ⁇ -C 8 alkyl optionally substituted with one C ⁇ -C 6 alkoxy, thiophene or furan group, C ⁇ -C 6 haloalkyl, C 3 -C 8 cycloalkyl, C0 2 R 23 , C 2 -C 6 alkenyl optionally substituted with phenyl, benzyl optionally substituted with any combination of one to three halogen atoms, one to three C ⁇ -C 4 alkyl groups, one to three C x -C 4 haloalkyl groups, one to three C ⁇ -C 4 alkoxy groups, one to three C ⁇ -C 4 haloalkoxy groups, one nitro group, one cyano group or one X 4 R 22 group, phenyl optionally substituted with any combination of one to three halogen atoms, one to three C ⁇ -C 4 alkyl groups, one to three
- R 35 and R 49 are each independently hydrogen or C ⁇ -C 6 alkyl and R 36 and R 50 are each independently hydrogen, cyano, C ⁇ -C 6 alkyl, S0 2 R 5X or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl,
- C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups or when R 3S and R 36 or R 49 and R 50 are taken together with the nitrogen atom to which they are attached, they form a 5- to 12-membered monocyclic or fused bicyclic, heterocyclic ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy, C ⁇ -C 4 haloalkoxy or C ⁇ -C 4 haloalkylsulfonyl groups; q is an integer of 0, 1 or 2;
- R 29 is hydrogen, C ⁇ -C 4 alkyl or C ⁇ -C 4 haloalkyl;
- R 24 , R 31 , R 4X and R 47 are each independently C ⁇ -C 4 alkyl, benzyl optionally substituted with one or more groups independently selected from halogen.
- R 23 , R 39 , R 40 , R 42 , R 43 , R 44 , R 46 and R 48 are each independently hydrogen, C 2 -C 6 alkenyl, C 3 -C 8 cycloalkyl, C ⁇ -C 8 alkyl optionally substituted with one or two C ⁇ -C 4 alkoxy groups, benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups, or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C-C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy and C ⁇ -C 4 haloalkoxy groups; or phenyl optionally substituted with one or
- a mixture of aluminum chloride (33.3 g, 25.0 mmol) in methylene chloride is cooled to about 5 °C, treated over one hour with p-methylanisole (31.6 g, 25.0 mmol) while maintaining the reaction mixture temperature below 10 °C, treated over 20 minutes with a solution of 2-chloro-5-nitrobenzoyl chloride (50.0 g, 22.7 mmol) in methylene chloride while maintaining the reaction mixture temperature below 10 °C, warmed to and stirred at room temperature for 60 minutes, and poured onto ice.
- the resultant aqueous mixture is treated with concentrated hydrochloric acid (50 mL) and extracted with methylene chloride.
- Ammonium hydroxide (350 mL of a 30% solution, 270 mmol) is added to a mixture of 2 ' -chloro-2-methoxy-5- methyl-5' -nitrobenzophenone (68.7 g, 22.5 mmol) and sulfur (7.57 g, 23.6 mmol) in N,N-dimethylformamide.
- the resultant reaction mixture is stirred at 80 °C for 19.5 hours, cooled to 40 °C, treated with additional ammonium hydroxide (50 mL of a 30% solution), stirred at 80 °C for 25 hours, cooled, and poured onto ice.
- the resultant aqueous mixture is filtered to obtain the title product as a yellow solid (63.5 g, 93.9%) which is identified by NMR spectral analyses .
- the organic extract is diluted with hexanes, washed with water, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain the title product as an orange foam (163 g, 98.8%) which is identified by NMR spectral analyses .
- CH 2 CH CH 2 CF, CH, H H H C0 2 CH 2 C ⁇ CH H 138-145
- a mixture of 3- (6-methoxy-m-tolyl) -5-nitro-l, 2- benzisoxazole (20.0 g, 0.0703 mol) in acetic acid (380 mL) is warmed, treated with a warm solution of tin(II) chloride dihydrate (47.4 g, 0.210 mol) in concentrated hydrochloric acid (110 mL) , refluxed for one hour, cooled to 10 °C, and concentrated in vacuo to obtain a gum.
- the gum is added to water with stirring to obtain a slurry.
- the slurry is treated with 80 g of 50% sodium hydroxide solution, stirred at 60 °C to 80 °C over one hour, cooled, and decanted to obtain a residue.
- a mixture of the residue in ethanol is treated with potassium hydroxide (10 g), heated overnight, cooled to room temperature, neutralized with hydrochloric acid, and concentrated in vacuo to obtain a residue.
- the residue is diluted with ethyl acetate and filtered.
- the filtrate is concentrated in vacuo and chromatographed using silica gel and a 2% ethyl acetate in methylene chloride solution to give the title products as semi-solids which are identified by elemental and mass spectral analyses .
- the resultant aqueous mixture is diluted with acetone, concentrated in vacuo, diluted with water, and filtered to obtain a solid.
- the solid is washed with water and dried in a vacuum oven at 60 °C to give the title product as a yellow solid which is identified by mass spectral analysis.
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Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU93925/98A AU9392598A (en) | 1997-09-17 | 1998-09-15 | Substituted 3(-1,2-benzisothiazol or isoxazol-5 yl)-substituted pyrimidine as herbicides |
JP2000511765A JP2001516758A (ja) | 1997-09-17 | 1998-09-15 | 除草剤としての置換3(−1,2−ベンズイソチアゾールまたはイソオキサゾール−5イル)−置換ピリミジン |
SK355-2000A SK3552000A3 (en) | 1997-09-17 | 1998-09-15 | Substituted 3-(1,2-benzisothiazol or isoxazol-5-yl)-substituted pyrimidine as herbicides |
BR9813017-0A BR9813017A (pt) | 1997-09-17 | 1998-09-15 | Composto, processo para o controle de espécies vegetais não desejáveis, composição herbicida, composto intermediário, e, processo para a preparação de um composto |
KR20007002805A KR20010030612A (en) | 1997-09-17 | 2000-03-16 | Substituted 3(-1,2-benzisothiazol or isoxazol-5 yl)-substituted pyrimidine as herbicides |
BG104336A BG104336A (en) | 1997-09-17 | 2000-04-13 | Substituted 3(-1,2-benzisothiazol or isoxazol-5-yl)-substituted pyrimidine as herbicides |
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US93145197A | 1997-09-17 | 1997-09-17 | |
US12883198A | 1998-08-04 | 1998-08-04 | |
US08/931,451 | 1998-08-04 | ||
US09/128,831 | 1998-08-04 |
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PCT/US1998/019251 WO1999014216A1 (en) | 1997-09-17 | 1998-09-15 | Substituted 3(-1,2-benzisothiazol or isoxazol-5 yl)-substituted pyrimidine as herbicides |
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EP (1) | EP0908457B1 (zh) |
JP (1) | JP2001516758A (zh) |
KR (1) | KR20010030612A (zh) |
CN (1) | CN1273585A (zh) |
AR (3) | AR015168A1 (zh) |
AT (1) | ATE227721T1 (zh) |
AU (2) | AU9392598A (zh) |
BG (1) | BG104336A (zh) |
BR (1) | BR9813017A (zh) |
CA (1) | CA2246221A1 (zh) |
CZ (1) | CZ2000861A3 (zh) |
DE (1) | DE69809370T2 (zh) |
ES (1) | ES2185118T3 (zh) |
HU (1) | HUP0004477A3 (zh) |
IL (1) | IL125947A0 (zh) |
MX (1) | MXPA00002661A (zh) |
NZ (1) | NZ331825A (zh) |
PL (1) | PL339350A1 (zh) |
SK (1) | SK3552000A3 (zh) |
TR (1) | TR200000679T2 (zh) |
TW (1) | TW474927B (zh) |
WO (1) | WO1999014216A1 (zh) |
YU (1) | YU15800A (zh) |
ZA (1) | ZA988435B (zh) |
Cited By (11)
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WO2000049016A1 (en) * | 1999-02-16 | 2000-08-24 | American Cyanamid Company | Process for the preparation of 6-(perfluoroalkyl)uracil compounds |
WO2002020531A2 (de) * | 2000-09-08 | 2002-03-14 | Basf Aktiengesellschaft | Verfahren zur herstellung anellierter tetrahydro-[1h]-triazole |
WO2003087072A1 (fr) * | 2002-03-29 | 2003-10-23 | Mochida Pharmaceutical Co., Ltd. | Agent therapeutique destine a des troubles endotheliaux |
US8673925B1 (en) | 2013-04-09 | 2014-03-18 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
US8940744B2 (en) | 2012-09-10 | 2015-01-27 | Principia Biopharma Inc. | Pyrazolopyrimidine compounds as kinase inhibitors |
US8962831B2 (en) | 2011-05-17 | 2015-02-24 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
US9376438B2 (en) | 2011-05-17 | 2016-06-28 | Principia Biopharma, Inc. | Pyrazolopyrimidine derivatives as tyrosine kinase inhibitors |
US10092569B2 (en) | 2014-02-21 | 2018-10-09 | Principia Biopharma Inc. | Salts and solid form of a BTK inhibitor |
US10485797B2 (en) | 2014-12-18 | 2019-11-26 | Principia Biopharma Inc. | Treatment of pemphigus |
US11155544B2 (en) | 2015-06-24 | 2021-10-26 | Principia Biopharma Inc. | Heterocycle comprising tyrosine kinase inhibitors |
US11872229B2 (en) | 2016-06-29 | 2024-01-16 | Principia Biopharma Inc. | Modified release formulations of 2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile |
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KR20020000140A (ko) * | 1999-02-16 | 2002-01-04 | 스타르크, 카르크 | 1,3-옥사진-6-온 및 우라실의 제조 방법 및 그에 사용되는제조 중간체 |
US6706663B2 (en) | 2000-04-17 | 2004-03-16 | Wyeth | Herbicidal 3-heterocyclic substituted benzisothiazole and benzisoxazole compounds |
KR100934256B1 (ko) | 2001-08-30 | 2009-12-28 | 알리자임 테라퓨틱스 리미티드 | 리파제 억제 활성을 갖는 티에노(1,3)옥사진-4-온 |
HUE027607T2 (en) | 2002-10-30 | 2016-10-28 | Basf Se | Amino-benzene sulfonic acid amides and their preparation |
ES2770550T3 (es) | 2011-05-17 | 2020-07-02 | Univ California | Inhibidores de quinasa |
DE102013226249A1 (de) * | 2013-12-17 | 2015-06-18 | Wacker Chemie Ag | Polyetherreste aufweisende Organopolysiloxangele |
EP3648605A1 (en) * | 2017-07-03 | 2020-05-13 | Bayer CropScience Aktiengesellschaft | Novel isothiazolo-based bicycles, processes for their preparation and their use as herbicides and/or plant growth regulators |
CN109776302A (zh) * | 2017-11-13 | 2019-05-21 | 中国科学院化学研究所 | 一种由木质素为甲基源制备重要化学品的方法 |
CN114276287B (zh) * | 2021-12-27 | 2023-10-03 | 浙江工业大学 | N-(取代苄氧基)酰胺类化合物及其制备方法和应用 |
CN116354953B (zh) * | 2022-12-31 | 2024-07-16 | 西北农林科技大学 | 含苯并噻唑类化合物的除草组合物 |
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Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000049016A1 (en) * | 1999-02-16 | 2000-08-24 | American Cyanamid Company | Process for the preparation of 6-(perfluoroalkyl)uracil compounds |
WO2002020531A2 (de) * | 2000-09-08 | 2002-03-14 | Basf Aktiengesellschaft | Verfahren zur herstellung anellierter tetrahydro-[1h]-triazole |
WO2002020531A3 (de) * | 2000-09-08 | 2003-01-03 | Basf Ag | Verfahren zur herstellung anellierter tetrahydro-[1h]-triazole |
WO2003087072A1 (fr) * | 2002-03-29 | 2003-10-23 | Mochida Pharmaceutical Co., Ltd. | Agent therapeutique destine a des troubles endotheliaux |
US8962831B2 (en) | 2011-05-17 | 2015-02-24 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
US9376438B2 (en) | 2011-05-17 | 2016-06-28 | Principia Biopharma, Inc. | Pyrazolopyrimidine derivatives as tyrosine kinase inhibitors |
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US9994576B2 (en) | 2012-09-10 | 2018-06-12 | Principia Biopharma Inc. | Substituted pyrazolo[3,4-d]pyrimidines as kinase inhibitors |
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Also Published As
Publication number | Publication date |
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AU9392598A (en) | 1999-04-05 |
MXPA00002661A (es) | 2001-10-31 |
KR20010030612A (en) | 2001-04-16 |
PL339350A1 (en) | 2000-12-18 |
YU15800A (sh) | 2002-11-15 |
BG104336A (en) | 2001-09-28 |
EP0908457A1 (en) | 1999-04-14 |
DE69809370D1 (de) | 2002-12-19 |
IL125947A0 (en) | 1999-04-11 |
DE69809370T2 (de) | 2003-03-27 |
CN1273585A (zh) | 2000-11-15 |
AU737864B2 (en) | 2001-08-30 |
CA2246221A1 (en) | 1999-03-17 |
EP0908457B1 (en) | 2002-11-13 |
HUP0004477A2 (hu) | 2001-02-28 |
NZ331825A (en) | 2000-04-28 |
AU8423998A (en) | 1999-04-01 |
CZ2000861A3 (cs) | 2000-08-16 |
ES2185118T3 (es) | 2003-04-16 |
ZA988435B (en) | 2000-03-15 |
BR9813017A (pt) | 2000-08-15 |
HUP0004477A3 (en) | 2002-01-28 |
SK3552000A3 (en) | 2001-01-18 |
ATE227721T1 (de) | 2002-11-15 |
JP2001516758A (ja) | 2001-10-02 |
AR015168A1 (es) | 2001-04-18 |
TR200000679T2 (tr) | 2000-08-21 |
AR021500A2 (es) | 2002-07-24 |
TW474927B (en) | 2002-02-01 |
AR021081A2 (es) | 2002-06-12 |
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